N-(tert-Butyl)thiourea → Methyl 2-[(1,1-dimethylethyl)amino]-5-(2-chlorophenyl)-4-thiazolecarboxylate

HRID 359299Notes

Reaction equation

HRID 359299 reaction equation
[C:1]([NH:5][C:6]([NH2:8])=[S:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[C:11](=O)[C:12]([O:14][CH3:15])=[O:13]>CO>[CH3:2][C:1]([NH:5][C:6]1[S:7][C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:11]([C:12]([O:14][CH3:15])=[O:13])[N:8]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 737374N-(tert-Butyl)thioureaHCID 20064768HCID 20064768, compound

Product 1

HCID 20064761Methyl 2-[(1,1-dimethylethyl)amino]-5-(2-chlorophenyl)-4-thiazolecarboxylateYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 50 ml methanol and 4 g (30 mmol) of tert-butyl thiourea. With this mixture stirred and cooled in an ice bath, there was added over a 5-minute period 7.41 g of (30 mmol) methyl 3-chloro-3-(o-chlorophenyl)pyruvate. The reaction mixture was refluxed for 16 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure to yield 9.18 g of a yellow solid which became a hard, glass-like material. This material was recrystallized from an acetone-water solution to yield 7.0 g of a yellow solid product (m.p.=159°-161° C.) identified in Table I.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe reaction mixture was refluxed for 16 hours
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2799709fefae4134b5cf1b00927133fd
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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