Phosgene → HCID 13089293, compound

HRID 1154572Notes

Reaction equation

HRID 1154572 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:13](Cl)(Cl)=[O:14]>N1C=CC=CC=1>[C:7]1([C:5]2[N:6]=[C:2]([NH:1][C:13]([NH:1][C:2]3[S:3][CH:4]=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:6]=3)=[O:14])[S:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 403022-Amino-4-phenylthiazole

Product 1

HCID 13089293HCID 13089293, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

Into 50 ml of a dry pyridine solution containing 7.5 g of 2-amino-4-phenylthiazole, 4.8 g of phosgene was absorbed under cooling (about 5° C.). The temperature of the mixture was then allowed to rise to room temperature. To this solution, 7.5 g of 2-amino-4-phenylthiazole was added further. The mixture was stirred overnight. The pyridine was removed under reduced pressure and the residue was converted to powder in methyl alcohol. The powder was then recrystallized from an N,N-dimethylformamide/methyl alcohol mixed solvent to obtain 8.5 g of N,N'-bis(4-phenylthiazol-2-yl)urea.

Workup

  1. customwas absorbed
  2. customto rise to room temperature
  3. additionTo this solution, 7.5 g of 2-amino-4-phenylthiazole was added further
  4. customThe pyridine was removed under reduced pressure
  5. customThe powder was then recrystallized from an N,N-dimethylformamide/methyl alcohol mixed solvent

Sources & evidence

ORD record
ord-914ffac6a6694fa2a9ebe4bca5479b9c
Source dataset
uspto-grants-1984_12
Patent number
US04490393

Reaction notes

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