4,5-Dihydro-2-thiazolamine → HCID 19886455, compound

HRID 654829Notes

Reaction equation

HRID 654829 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)[C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.[NH2:21][C:22]1[S:23][CH2:24][CH2:25][N:26]=1>CN(C=O)C.O>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]2[N:26]3[C:22]([S:23][CH2:24][CH2:25]3)=[N:21][C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:5][CH:6]=1)#[N:11]

Participants

5

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 19886451HCID 19886451, compound

Product 1

HCID 19886455HCID 19886455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.8 g of 1-bromo-2-oxo-1,2-di(4-cyanophenyl)ethane, prepared as described above in part (b) and 3.8 g of 2-aminothiazoline in 70 ml of DMF was stirred at room temperature for 18 hours. The reaction mixture was diluted with cold water, and the precipitated product was filtered and dried in vacuum. The material was suspended in 200 ml of toluene, 125 mg of p-toluenesulfonic acid was added, and the mixture was refluxed for 2 hours with removal of water. After cooling, the crude product was filtered and recrystallized twice from acetic acid to afford the part (c) title compound, 1.3 g, m.p. 255°-260°; Analysis: C19H12N4S.0.5AcO; Theory; C 67.03%, H 3.91%, N 15.64%; found C: 67.03% H: 3.96%, N: 15.04%.

Workup

  1. customprepared
  2. filtrationthe precipitated product was filtered
  3. customdried in vacuum
  4. addition125 mg of p-toluenesulfonic acid was added
  5. temperaturethe mixture was refluxed for 2 hours with removal of water
  6. temperatureAfter cooling
  7. filtrationthe crude product was filtered
  8. customrecrystallized twice from acetic acid

Sources & evidence

ORD record
ord-6531c41e4eaa46c38b074a80b18e6ec1
Source dataset
uspto-grants-1992_07
Patent number
US05134150

Reaction notes

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