32326-25-3|5-Methoxyisoxazol-3-amine| Ambeed

CAS No. :	32326-25-3
Formula :	C₄H₆N₂O₂
M.W :	114.10
SMILES Code :	COC1=CC(=NO1)N
MDL No. :	MFCD09701967
InChI Key :	PVDLBNRYTGXVPC-UHFFFAOYSA-N
Pubchem ID :	11007859

Safety of [ 32326-25-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 32326-25-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 32326-25-3 ]

[ 32326-25-3 ] Synthesis Path-Downstream 1~14

1
[ 333-20-0 ]
[ 541-41-3 ]
[ 32326-25-3 ]
[ 150215-07-9 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 6423 - 6426.
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1701 - 1707.

2
[ 333-20-0 ]
[ 501-53-1 ]
[ 32326-25-3 ]
[ 150215-09-1 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 6423 - 6426.
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1701 - 1707.

3
[ 333-20-0 ]
[ 79-22-1 ]
[ 32326-25-3 ]
[ 149196-71-4 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 6423 - 6426.
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1701 - 1707.

4
[ 333-20-0 ]
[ 1885-14-9 ]
[ 32326-25-3 ]
[ 150215-08-0 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 6423 - 6426.
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1701 - 1707.

5
[ 15732-02-2 ]
[ 32326-25-3 ]

Yield	Reaction Conditions	Operation in experiment
70.6%	With sodium hydroxide; hydroxylamine hydrochloride; In methanol; water;	(B) To a solution of hydroxylamine hydrochloride (1.55 g, 22.3 mmol) in water (3.41 ml) was added 8N aqueous sodium hydroxide solution (3.35 ml; 26.8 mmol) under stirring at room temperature. The temperature was elvated to 45 C. and a solution of 3,3-dimethoxyacrylonitrile (2.27 g; 20.1 mmol) in methanol (5.50 ml) was added dropwise for 30 minutes and then the mixture was stirred at the same temperature for 1 hour. After disappear of 3,3-dimethoxyacrylonitrile was apparent, 8N sodium hydroxide (1.25 ml; 10.1 mmol) was added to the mixture at the same temperature and the temperature was elevated to 60 C. The mixture was stirred for 6 hours. After the reaction was completed, the reaction mixture was directly concentrated (60 C./19 mmHg: until an inorganic compound was begun to precipitate). The obtained concentrate was extracted with ethyl acetate (5 ml*3) and the extract was dried over sodium sulfate and concentrated and the residue was dried under reduced pressure to give 3-amino-5-methoxyisoxazole (1.63 g; yield 70.6%) as white crystals. m.p. 82-83 C. (hexane-ethyl acetate) NMR delta (CDCl3): 3.93(5H,bs,CH3 +NH2), 4.81(1H,s,H-4) NMR delta (CDCl3 +D2 O): 3.93 (3H,s,CH3), 4.83(1H,s,H-4) IR (CHL3)cm-1: 3840, 1628, 1487. Anal. Calcd. for C4 H6 N2 O2: C,42.11;H,5.30; N 24.55(%). Found: C,41.74; H, 5.06; N, 24.35(%).

References: [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1701 - 1707.
[2]Patent: US5585494,1996,A .

6
[2-methyl-1-(pyrazolidine-1-carbonyl)-butyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
[ 75-44-5 ]
[ 32326-25-3 ]
{1-[2-(5-methoxy-isoxazol-3-ylcarbamoyl)-pyrazolidine-1-carbonyl]-2-methyl-butyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1048 - 1050.

7
[ 541-41-3 ]
[ 32326-25-3 ]
[ 150215-07-9 ]

Yield	Reaction Conditions	Operation in experiment
78.9%	In acetonitrile;	Example 2 A suspension of ethyl chloroformate (124 mul; 1.29 mmol) and potassium thiocyanate (136 mg; 1.40 mmol) in acetonitrile (1.08 ml) was treated with <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (123 mg; 1.08 mmol) in the same manner as in Example 1 except that ethyl chloroformate was substituted for methyl chloroformate to give methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3yl)acetate (209 mg; yield 78.9%). m.p. 110-112 C. (MeOH) NMR delta (CDCl3): 1.38(3H.t.CH3) 3.73(3H.s.COOCH3) 3.97(2H.s.CH2 COOCH3) 4.39(2H.q. CH2) 10.45(1H.bs.NH) IR(CHCl3)cm-1: 3406, 1732, 1564. Anal. Calcd. for C8 H11 N3 O4 S: C,39.18; H, 4.52; N, 17.13(%). Found: C,39.16; H,4.40; N,17.18(%).

References: [1]Patent: US5585494,1996,A .

8
[ 501-53-1 ]
[ 32326-25-3 ]
[ 150215-09-1 ]

Yield	Reaction Conditions	Operation in experiment
24.9%	In acetonitrile;	Example 4 A suspension of benzyloxycarbonyl chloride (285 mul; 2.00 mmol) and potassium thiocyanate (210 mg; 2.17 mmol) in acetonitrile (1.67 ml) was treated with <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (190 mg; 1.67 mmol) in the same manner as in Example 1. Since no crystalization was occurred when the reaction mixture was poured into ice-water, the mixture was extracted with ethyl acetate and the extract was purified by silica gel column chromatography to give methyl 2-(5-benzyloxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (128 mg; yield 24.9%). m.p. 121-123 C. (MeOH) NMR delta (CDCl3): 3.70 (3H.s.CH3) 3.85(2H.s.CH2) 5.33(2H.s.CH2 Ph) 7.35-7.45(5H.m. Ph) 9.96(1H.bs.NH) IR(CHCl3)cm-1: 3404, 1736, 1564. Anal. Calcd. for C13 H13 N3 O4 S: C,50.81;H,4.26;N, 13.67(%). Found: C,50.85; H,4.27; N,13.43(%).

References: [1]Patent: US5585494,1996,A .

9
[ 1885-14-9 ]
[ 32326-25-3 ]
[ 150215-08-0 ]

Yield	Reaction Conditions	Operation in experiment
57.4%	In acetonitrile;	Example 3 A suspension of phenyl chloroformate (232 mul; 1.85 mmol) and potassium thiocyanate (195 mg; 2.00 mmol) in acetonitrile (1.54 ml) was treated with <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (170 mg; 1.49 mmol) in the same manner as in Example 1 except that phenyl chloroformate was substituted for methyl chloroformate to give methyl 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl) acetate (251 mg; yield 57.4%). m.p. 162-164 C. (MeOH) NMR delta (CDCl3): 3.66(3H.s. CH3) 3.99(2H.s.CH2) 7.13-7.48(5H.m.ph) 10.87(1H.bs.NH) IR(CHCl3)cm-1: 3432, 1743, 1576. Anal. Calcd. for C12 H11 N3 O4 S C,49.14; H,3.78; N,14.33(%). Found: C,48.81; H,3.79; N,14.31(%).

References: [1]Patent: US5585494,1996,A .

10
[ 79-22-1 ]
[ 32326-25-3 ]
[ 149196-71-4 ]

Yield	Reaction Conditions	Operation in experiment
80.6%	In acetonitrile;	Example 1 A suspension of methyl chloroformate (167 mul; 2.16 mmol) and potassium thiocyanate (227 mg; 2.34 mmol) in acetonitrile (1.80 ml) was stirred at 70 C. for 30 minutes, and then <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (205 mg; 1.80 mmol) was added to the suspension under stirring and ice-cooling. After stirring for 10 minutes at the same temparature and then for 15 minutes at room temperature, the reaction mixture was poured into ice-water (18ml). The precipitates formed were filtered off, washed with water, then with ether and dried under reduced pressure to give methyl 2-(5-methoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (334 mg, yield 80.6%). m.p. 167-169 C. (MeOH) NMR delta (CDCl3): 3.73 (3H. s. COOCH3) 3.95 (3H. s. NHCOOCH3) 3.97 (2H. s. CH2) 10.50 (1H. bs. NH) IR (CHCL3)cm-1: 3406, 1736, 1549. Anal, Calcd, for C7 H9 N3 O4 S: C,36.36; H, 3.92; N,18.17(%). Found: C,36.40; H,3.94; N,18.11(%).

References: [1]Patent: US5585494,1996,A .

11
[ 79-22-1 ]
[ 32326-25-3 ]
[5-Amino-3-(1,2,4-thiadiazole)]acetic acid, methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	(A) A solution of methyl chloroformate (53.3 mul, 6.9010-1 mmol) and potassium thiocyanate (72.6 mg, 7.4710-1 mmol) in anhydrous tetrahydrofuran (575 mul) was stirred for 1 hour at 70 C., and then <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (65.6 mg, 57.5*10-1 mmol) was added to the reaction mixture under ice-cooling and stirring. The mixture was stirred for 30 minutes at the same temperature and further for 12 hours at room temperature. After the reaction was completed, resdiual potassium thiocyanate was decomposed by adding water (72.6 mul) to the reaction mixture at the same temperature and then resdiual potassium thiocyanate was disintegrate by stirring for 3 hours to give methyl (5-amino-1,2,4-thiadiazol-3-yl)acetate.

References: [1]Patent: US5585494,1996,A .

12
[ 532-55-8 ]
[ 32326-25-3 ]
methyl 2-(5-phenylcarbonylamino-1,2,4-thiadiazol-3-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.7%	In tetrahydrofuran; ethanol;	Example 15 <strong>[32326-25-3]<strong>[32326-25-3]3-amino-5-methoxyisoxazol</strong>e</strong> (1.2 g) was dissolved in tetrahydrofuran (10 ml) and benzoylisothiocyanate (2.2 g) was added dropwise thereto at 2-3 C. After the mixture was stirred for 1 hour, the reaction mixture was poured into ice-water and then the formed crystals were filtered off. After washing with water and isopropylether, the crystals was dissloved in ethanol (50 ml) with warming. The solution was concentrated under reduced pressure to give methyl 2-(5-benzoylamino-1,2,4-thiadiazol-3-yl)acetate (1.6 g, 57.7%). m.p.143-144.5C. NMR delta (CDCl3): 3.68(3H,s,--COOOCH3), 3.81(2H,s,CH2), 7.05-8.0(5H,m, --C6 H5) IR(KBr)cm-1: 1720, 1660, 1540.

References: [1]Patent: US5585494,1996,A .

13
[ 122-51-0 ]
[ 32326-25-3 ]
5-methoxy-3-(1H-tetrazol-1-yl)isoxazole [ No CAS ]

References: [1]New Journal of Chemistry,2015,vol. 39,p. 2028 - 2041.

14
C₂₀H₂₀F₃NO₄S [ No CAS ]
[ 32326-25-3 ]
1-(2-(5-methoxyisoxazol-3-yl-amino)ethyl)-7-(trifluoromethyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydrogencarbonate; In methanol; for 8.0h;Reflux;	In a reaction flask equipped with a stirrer, a condenser and a thermometer,4.27 g (0.01 mol) of Intermediate IV-2, 2.00 g (0.02 mol) of potassium bicarbonate,30ml of methanol and 1.14g (0.01mol) <strong>[32326-25-3]5-methoxy-3-aminoisoxazole</strong>, the reaction was refluxed 8h,The reaction was complete by TLC, insolubles were filtered off, the solvent was evaporated and the residue was chromatographed on silica gel,Compound I-5 was obtained as a white solid with a yield of 88% and a purity of 99.7% (HPLC normalization method)

References: [1]Patent: CN103804367,2016,B .Location in patent: Paragraph 0099-0101.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Nomenclature of Ethers • Petasis Reaction • Preparation of Amines • Preparation of Ethers • Reactions of Amines • Reactions of Ethers • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 32326-25-3 ]

Amines

A206388 [1750-42-1]

Isoxazol-3-amine

Similarity: 0.73

A241010 [1072-67-9]

5-Methylisoxazol-3-amine

Similarity: 0.62

A165100 [19754-80-4]

5-Ethylisoxazol-3-amine

Similarity: 0.57

A112554 [13999-39-8]

3-Amino-4,5-dimethylisoxazole

Similarity: 0.57

A112824 [55809-36-4]

3-Amino-5-tert-butylisoxazole

Similarity: 0.53

Related Parent Nucleus of
[ 32326-25-3 ]

Isoxazoles

A206388 [1750-42-1]

Isoxazol-3-amine

Similarity: 0.73

A241010 [1072-67-9]

5-Methylisoxazol-3-amine

Similarity: 0.62

A165100 [19754-80-4]

5-Ethylisoxazol-3-amine

Similarity: 0.57

A112554 [13999-39-8]

3-Amino-4,5-dimethylisoxazole

Similarity: 0.57

A448611 [288-14-2]

Isoxazole

Similarity: 0.53

Precautionary Statements-General
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 32326-25-3 ] Synthesis Path-Downstream 1~14

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[ 32326-25-3 ]

Amines

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[ 32326-25-3 ]

Isoxazoles

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Product Details of [ 32326-25-3 ]

Safety of [ 32326-25-3 ]

Application In Synthesis of [ 32326-25-3 ]

[ 32326-25-3 ] Synthesis Path-Downstream 1~14

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 32326-25-3 ]

Amines

Related Parent Nucleus of [ 32326-25-3 ]

Isoxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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Total Compounds Calculator

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Related Functional Groups of
[ 32326-25-3 ]

Related Parent Nucleus of
[ 32326-25-3 ]