Chloroacetaldehyde → (4-Methoxy-phenyl)thiazol-2-yl-amine

HRID 1713653

Reaction equation

HRID 1713653 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.Cl[CH2:14][CH:15]=O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[S:11][CH:14]=[CH:15][N:12]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 6675494-Thioureidoanisole

Product 1

HCID 956680(4-Methoxy-phenyl)thiazol-2-yl-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4-methoxy-phenyl)-thiourea (3.0 g, 16.5 mmol) and a 45% aqueous solution of chloroacetaldehyde (12 mL, 82.4 mmol, 5.0 equiv) in EtOH (23 mL) is heated to reflux for 1 h. The resulting dark orange solution is allowed to cool to RT and concentrated in vacuo. NaHCO3 is then added to the oily residue until CO2 evolution subsides and a beige precipitate forms. The product is collected by vacuum filtration, washed thoroughly with water (600 mL), and dried in vacuo. Title compound: ES-MS: 207.0 [M+H]+; single peak at tR=5.32 min (System 1); Rf=0.17 (CH2Cl2/MeOH, 95/5).

Workup

  1. temperatureto reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. additionNaHCO3 is then added to the oily residue until CO2 evolution subsides
  4. filtrationThe product is collected by vacuum filtration
  5. washwashed thoroughly with water (600 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-73cbf53bae11469aa911c9e263bd879e
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Linked notes

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