Phenyl isocyanate → HCID 9841584, compound

HRID 618691Notes

Reaction equation

HRID 618691 reaction equation
[CH3:1][NH:2][C:3]([O:5][CH2:6][C@@H:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][NH:8]1)=[S:4].[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH3:1][NH:2][C:3]([O:5][CH2:6][C@@H:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[C:24]([NH:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25])=[S:4]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 10220330HCID 10220330, compound

Product 1

HCID 9841584HCID 9841584, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(N-Methyl-thiocarbamoyloxymethyl) -1,2,3,4-tetrahydroisoquinoline (1.0 g, 4.94 mmol) dissolved in 20 mL dichloromethane was combined with PhNCO (1.0 g) and stirred for 24 h at rt. The reaction mixture was evaporated and the crude product was purified by column-chromatography (SiO2, hexanes:EtOAc=3:2) to provide the product as white solid (1.7 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude product was purified by column-chromatography (SiO2, hexanes:EtOAc=3:2)

Sources & evidence

ORD record
ord-11f4da7b86214811babb78301ca10a83
Source dataset
uspto-grants-1999_09
Patent number
US05955471

Reaction notes

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