Methyl chloroacetate → HCID 87676872, compound

HRID 1820620Notes

Reaction equation

HRID 1820620 reaction equation
CO[Na].[N:4]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[C:5]=[S:6].[NH2:15][C:16]#[N:17].Cl[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CO>[CH3:23][O:22][C:20]([C:19]1[S:6][C:5]([NH:4][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[N:17][C:16]=1[NH2:15])=[O:21]

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 9864CyanamideHCID 17626Benzonitrile, 4-isothiocyanato-HCID 178418582HCID 178418582, compound

Product 1

HCID 87676872HCID 87676872, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of MeONa in methanol (25% by wt., 2.0 mL, 9.36 mmol) was added dropwise to a suspension of 4-isothiocyanato-benzonitrile Compound 4a (1.0 g, 6.24 mmol) and NH2CN (0.289 g, 6.87 mmol) in methanol (25 mL) at 0° C. The mixture was stirred at r.t. until Compound 4a was no longer detected (about 3 hrs). Methyl chloroacetate (0.657 mL, 7.49 mmol) was added at r.t. and the mixture was stirred at 50-60° C. for 3 hrs, then at r.t. overnight. The mixture was evaporated to dryness in vacuo, then the residual solid was thoroughly washed with water, methylene chloride and a small amount of methanol to give 4-amino-2-(4-cyano-phenylamino)-thiazole-5-carboxylic acid methyl ester Compound 4b (1.06 g, 62%) as a yellow powder. MS 273 (M−H+)

Workup

  1. custom(about 3 hrs)
  2. customat r.t.
  3. customovernight
  4. customThe mixture was evaporated to dryness in vacuo
  5. washthe residual solid was thoroughly washed with water, methylene chloride

Sources & evidence

ORD record
ord-fa93d7cc5b4a43578a54a193c28e96c0
Source dataset
uspto-grants-2009_10
Patent number
US07605154B2

Reaction notes

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