Ammonia → HCID 12923103, compound

HRID 1702590Notes

Reaction equation

HRID 1702590 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12](=O)[CH2:13]Cl)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:20][NH:21][C:22]([NH2:24])=[S:23].N.O>C(O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]3[N:24]=[C:22]([NH:21][CH3:20])[S:23][CH:13]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 2723704MethylthioureaHCID 13050589HCID 13050589, compound

Product 1

HCID 12923103HCID 12923103, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.43 g portion of 4-(4-chlorobenzyloxy)phenacyl chloride and 495 mg of 1-methylthiourea were stirred in 30 ml of ethanol at 70° C. for 30 minutes. After cooling, 10 ml of aqueous ammonia was added to stir at room temperature for 10 minutes. Water was added to extract with ethyl acetate. After washing with water and drying, the ethyl acetate was distilled off, thus yielding 1.47 g (89.1%) of 4-[4-(4-chlorobenzyloxy)phenyl]-2-methylaminothiazole. Recrystallization from ethyl acetate afforded crystals of m.p. 158°-159° C.

Workup

  1. temperatureAfter cooling
  2. extractionto extract with ethyl acetate
  3. washAfter washing with water
  4. customdrying
  5. distillationthe ethyl acetate was distilled off

Sources & evidence

ORD record
ord-285221a226a24498915dcb8f1b105594
Source dataset
uspto-grants-1982_09
Patent number
US04348403

Reaction notes

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