Methyl chloroacetate → Methyl 4-amino-2-anilino-1,3-thiazole-5-carboxylate

HRID 1820619Notes

Reaction equation

HRID 1820619 reaction equation
C[O-].[Na+].[N:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[C:5]=[S:6].[NH2:13][C:14]#[N:15].Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CO>[CH3:21][O:20][C:18]([C:17]1[S:6][C:5]([NH:4][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:15][C:14]=1[NH2:13])=[O:19]

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 7673Phenyl IsothiocyanateHCID 9864CyanamideHCID 10942334Sodium Methoxide

Product 1

HCID 26342993Methyl 4-amino-2-anilino-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A 0.5 M solution of sodium methoxide in methanol (44.4 mL, 22.19 mmol) was added dropwise to a suspension of isothiocyanato-benzene Compound 3a (2.0 g, 14.79 mmol) and NH2CN (0.684 g, 16.27 mmol) in methanol (50 mL) at 0° C. The mixture was stirred at r.t. until Compound 3a was no longer detected (about 3 hrs). Methyl chloroacetate (1.56 mL, 17.75 mmol) was added at r.t. and the mixture was warmed to 50-60° C. and stirred at 50-60° C. for about 3 hrs, then stirred at r.t. overnight. The mixture was evaporated to dryness in vacuo and the resultant solid was thoroughly washed with water, methylene chloride and a small amount of methanol to give 4-amino-2-phenylamino-thiazole-5-carboxylic acid methyl ester Compound 3b (1.12 g, 60%) as a yellow powder. MS 250 (M+H+), 248 (M−H+)

Workup

  1. custom(about 3 hrs)
  2. stirringstirred at r.t. overnight
  3. customThe mixture was evaporated to dryness in vacuo
  4. washthe resultant solid was thoroughly washed with water, methylene chloride

Sources & evidence

ORD record
ord-e1b281ef49c74c3eb7f4ca472b32a623
Source dataset
uspto-grants-2009_10
Patent number
US07605154B2

Reaction notes

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