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

HRID 267741Notes

Reaction equation

HRID 267741 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-5f2e8bf05d324149bd8c5426482a8799
Source dataset
uspto-grants-1976_03
Patent number
US03944567

Reaction notes

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