Water → HCID 10367681, compound

HRID 1587401Notes

Reaction equation

HRID 1587401 reaction equation
Cl.S1C=CN=C1.[NH2:7][C:8]1[S:9][C:10]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:12]=1.[H-].[Na+].[C:31]([N:39]=[C:40]=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>CN(C)C=O.C1(C)C=CC=CC=1>[C:31]([NH:39][C:40](=[S:41])[NH:7][C:8]1[S:9][C:10]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[N:12]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 68284Benzoyl isothiocyanateHCID 19757959HCID 19757959, compound

Product 1

HCID 10367681HCID 10367681, compoundYield 150.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of 2-amino-4,5-bis(4-methoxyphenyl)thiazole thiazole hydrochloride (35.7 g) in a mixture of N,N-dimethylformamide (60 ml) and toluene (60 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (4.58 g) in a mixture of N,N-dimethylformamide (60 ml) and toluene (60 ml) for 30 minutes at 0° C. with stirring. The reaction mixture was stirred at the same temperature for 30 minutes. A solution of benzoyl isothiocyanate (9.57 g) in a mixture of N,N-dimethylformamide (30 ml) and toluene (30 ml) was added dropwise to the above-mentioned reaction mixture at 0°~5° C., stirred for 1 hour and continued to stir at 5°~10° C. for 2 hours. Water (200 ml) was added thereto and the resulting mixture was extracted with ethyl acetate (200 ml). The extract was washed with water and brine. The resulting organic layer was dried and evaporated. The residue was crystallized from ethyl acetate to give 2-(3-benzoylthioureido)-4,5-bis( 4-methoxyphenyl)thiazole (41.9 g).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes
  2. additionwas added dropwise to the above-mentioned reaction mixture at 0°~5° C.
  3. stirringstirred for 1 hour
  4. stirringto stir at 5°~10° C. for 2 hours
  5. extractionthe resulting mixture was extracted with ethyl acetate (200 ml)
  6. washThe extract was washed with water and brine
  7. customThe resulting organic layer was dried
  8. customevaporated
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d8d48098dc454e4c97bfd613a24c5fe6
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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