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

HRID 1834128Notes

Reaction equation

HRID 1834128 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-2530a47f048948e1b5f427742e7bb7d0
Source dataset
uspto-grants-1978_01
Patent number
US04069231

Reaction notes

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