Thiourea → 5-Phenyl-thiazol-2-ylamine

HRID 2409899Notes

Reaction equation

HRID 2409899 reaction equation
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:3]=O.[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[C:5]1([C:2]2[S:13][C:12]([NH2:14])=[N:11][CH:3]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 108889012-Bromo-2-phenylacetaldehyde

Product 1

HCID 8731195-Phenyl-thiazol-2-ylamineYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of bromo-phenyl-acetaldehyde (1 g, 5 mmol), thiourea (0.64 g, 10 mmol) and ethanol (3.5 mL) was heated to reflux overnight. The mixture was then cooled to rt and the resulting yellow precipitate filtered. The precipitate was then washed with aqueous NaHCO3 solution (10 mL) and dried. Recrystallization from 30% methanol gave 5-phenylthiazol-2-amine (500 mg, 2.84 mmol, 56.5%) as a yellow solid. Anal. Calcd. for C9H8N2S m/z 176.2, found: 177.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.41 (m, 3H), 7.33 (m, 2H), 7.18 (m, 1H), 7.13 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe resulting yellow precipitate filtered
  4. washThe precipitate was then washed with aqueous NaHCO3 solution (10 mL)
  5. customdried
  6. customRecrystallization from 30% methanol

Sources & evidence

ORD record
ord-a2ddabafb8a14ed4ab357dbb48df8287
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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