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

HRID 1889187Notes

Reaction equation

HRID 1889187 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11]Br)=[CH:6][CH:5]=1.[NH2:15][C:16]([NH2:18])=[S:17].C(O)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:16]([NH2:18])[S:17][CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 2723790ThioureaHCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 2060012Methyl 4-(2-aminothiazol-4-yl)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-bromo-acetyl)-benzoic acid methyl ester (1 g, 3.89 mmol) and thiourea (0.29 g, 3.89 mmol) were taken isopropyl alcohol (100 ml) and refluxed for 10 minutes followed by addition of sodium carbonate (0.206 g, 1.94 mmol) and stirred for 30 minutes. Reaction mixture was cooled to room temperature and poured in water. The precipitate obtained was filtered off, washed with water and diethyl ether and dried under vacuum to afford 4-(2-amino-thiazol-4-yl)-benzoic acid methyl ester (0.500 g, 55%).

Workup

  1. temperaturerefluxed for 10 minutes
  2. customReaction mixture
  3. customThe precipitate obtained
  4. filtrationwas filtered off
  5. washwashed with water and diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-edd68001d0254201baf403bffba13558
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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