Thiourea → Methyl 4-(2-aminothiazol-4-yl)benzoate

HRID 2243045Notes

Reaction equation

HRID 2243045 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>CO>[NH2:18][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 2060012Methyl 4-(2-aminothiazol-4-yl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(bromoacetyl)benzoate (300 mg, 1.17 mmol) and thiourea 110 mg, 1.40 mmol) were taken in MeOH (5 ml) and refluxed for 2 hours. The precipitated product was collected by filtration, washed with MeOH and dried (260 g). MS (ESP): 235 (M+H+) for C11H10N2O2S; NMR: 3.87 (s, 3H), 7.38 (s, 1H), 7.90 (d, 2H), 8.01 (d, 2H).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with MeOH
  4. customdried (260 g)

Sources & evidence

ORD record
ord-b41dcbfe9fd54ee9a6a4006d75b52476
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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