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Chemical Structure| 136539-01-0 Chemical Structure| 136539-01-0

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Chemical Structure| 136539-01-0

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Product Details of [ 136539-01-0 ]

CAS No. :136539-01-0
Formula : C6H7ClN2O2S
M.W : 206.65
SMILES Code : CCOC(=O)C1=C(Cl)SC(N)=N1
MDL No. :MFCD08704623
InChI Key :JILQJAVCOAVWCC-UHFFFAOYSA-N
Pubchem ID :21780304

Safety of [ 136539-01-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 136539-01-0 ]

* 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 [ 136539-01-0 ]

[ 136539-01-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 136539-01-0 ]
  • [ 425392-44-5 ]
YieldReaction ConditionsOperation in experiment
100% With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 80℃; Tert-butyl nitrite (1.5 eq, 34.8 mmol) and copper (II) bromide (1.5 eq, 34.8) were dissolved in acetonitrile (180 mL). Ethyl 2-amino-5-chlorothiazole-4-carboxylate (1 eq, 23.2 mmol) in acetonitrile (60 mL) was added by dropping funnel over 45 min and upon complete addition the reaction stirred at 80 C overnight. The reaction was determined to be complete by TLC (4: 1 Hex/EtOAc). The reaction was concentrated in vacuo, taken up in NaHCCb, and extracted with EtOAc (50 mL x 3). The organics were collected and washed with brine (100 mL), dried with Na2S04, filtered and concentrated to give the title compound in quantitative yield.
46% With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 80℃; for 2.0h; A solution of ethyl 2-amino-5-chloro-l,3-thiazole-4-carboxylate (2.00 g, 9.678 mmol, 1.00 equiv), tert-butyl nitrite (1.20 g, 11.637 mmol, 1.20 equiv), cupric bromide (2.59 g, 11.596 mmol, 1.20 equiv) in acetonitrile (50 mL) was stirred for 2 h at 80 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (40:1) to give the title compound (1.2 g, 46%) as a white solid. LC-MS (ES, m/z): 270 [M+H]+.
With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 5 - 65℃; 16.2. 2-Bromo-5-chloro-thiazole-4-carboxylic acid ethyl esterTo a suspension of CuBr2 (250.8 mg) in CH3CN (4 mL) was added at 5C isopentyl nitrite (0.23 mL). After stirring for 5 min was added in portions at 5C intermediate 16.1. ELN145- 0048.2. (281.8 mg) and the reaction mixture was carefully heated to 65C for 1.5 h. The reaction mixture was evaporated to dryness, the residue diluted with H2O and stirred at RT for I h. The precipitate was filtrated and washed with H2O, CH2Cl2 (5x1.5 mL). The filtrate was evaporated, the residue taken up in Et2O (4 mL) and stirred at RT overnight. The mixture was filtrated, taken up in Hept (1.5 mL), stirred for 1 h again, filtrated and evaporated to dryness to give 224 mg of the desired product. 1H NMR δ, 4.46 (q, 2 H), 1.44 (t, 3 H).
 

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Technical Information

Categories

Related Functional Groups of
[ 136539-01-0 ]

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Esters

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Amines

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Related Parent Nucleus of
[ 136539-01-0 ]

Thiazoles

Chemical Structure| 1956341-60-8

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Similarity: 0.92

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