Phenyl Isothiocyanate → 4-Hydroxy-6-N-phenylthiocarbamoyl-4,5,6,7-tetrahydro-thieno[2,3-c]-pyridine

HRID 616891Notes

Reaction equation

HRID 616891 reaction equation
[OH:1][CH:2]1[CH2:7][NH:6][CH2:5][C:4]2[S:8][CH:9]=[CH:10][C:3]1=2.[C:11]1([N:17]=[C:18]=[S:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1.C(O)C>[OH:1][CH:2]1[CH2:7][N:6]([C:18](=[S:19])[NH:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][C:4]2[S:8][CH:9]=[CH:10][C:3]1=2

Participants

5

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 123370234,5,6,7-Tetrahydrothieno[2,3-c]pyridin-4-ol

Product 1

HCID 203668314-Hydroxy-6-N-phenylthiocarbamoyl-4,5,6,7-tetrahydro-thieno[2,3-c]-pyridineYield 79%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-4,5,6,7-tetrahydro-thieno[2,3-c]-pyridine (5.8 g; 37.4 mmoles) in benzene (60 cc) and 95% ethanol (30 cc) is added dropwise a mixture of phenyl isothiocyanate (5.05 g; 37.4 mmoles) in benzene (20 cc). After stirring during 2.5 hours at room temperature, the resulting precipitate is filtered off, washed with ether and dried in vacuo (M.p. = 168° C; yield: 79%).

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. washwashed with ether
  3. customdried in vacuo (M.p. = 168° C; yield: 79%)

Sources & evidence

ORD record
ord-3d69328eaf824cdc8b008681d392276f
Source dataset
uspto-grants-1978_02
Patent number
US04076819

Reaction notes

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