Phosgene → 4-Isocyanato-4,5,6,7-tetrahydro-1-benzothiophene

HRID 1282733Notes

Reaction equation

HRID 1282733 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.[C:12](Cl)(Cl)=[O:13]>C1(C)C=CC=CC=1>[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([N:11]=[C:12]=[O:13])[CH2:8][CH2:9][CH2:10][C:3]1=2

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 173886004,5,6,7-Tetrahydrobenzo[b]thiophen-4-amine hydrochloride

Product 1

HCID 205373014-Isocyanato-4,5,6,7-tetrahydro-1-benzothiophene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Alternatively, 5.7 grams of 4,5,6,7-tetrahydrobenzo[b]thien-4-amine hydrochloride is stirred in 20 ml. of toluene at 97°C., and phosgene is slowly introduced into the mixture via a capillary delivery tube. The mixture is heated to reflux temperature, and the flow of phosgene is continued until most of the amine hydrochloride disappears. The mixture is then filtered to remove unreacted amine hydrochloride, and the filtrate is evaporated to dryness under reduced pressure to give the 4,5,6,7-tetrahydrobenzo[b]thien-4-yl isocyanate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. filtrationThe mixture is then filtered
  4. customto remove unreacted amine hydrochloride
  5. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-62f617f715814833ab55fa33bba1039f
Source dataset
uspto-grants-1976_08
Patent number
US03972895

Reaction notes

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