Phosgene → Benzo[b]thiophene-3-sulfonyl isocyanate

HRID 1074369Notes

Reaction equation

HRID 1074369 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:2]1.C(N=[C:19]=[O:20])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O.[N-]=C=O>C1(C)C(C)=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([S:10]([N:13]=[C:19]=[O:20])(=[O:12])=[O:11])=[CH:2]1

Participants

7

Reactant 5

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 105034IsocyanateHCID 13178324HCID 13178324, compound

Product 1

HCID 13178325Benzo[b]thiophene-3-sulfonyl isocyanate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ten grams of benzothiophene-3-sulfonamide, 100 ml of xylene, 3 g. of butyl isocyanate and 0.1-0.3 g. of 1,4-diazabicyclo[2,2,2]octane in admixture were heated to reflux for one half hour after which phosgene was passed into the mixture for two hours at 125°. The reaction mixture was cooled, filtered and concentrated in vacuo to yield an oil (12 g.). Infrared analysis of this oil showed an absorption peak at 2250 cm-1 consistent for the desired isocyanate.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto yield an oil (12 g.)

Sources & evidence

ORD record
ord-52cd80b286ab4ee09f3fa3e9c731fc54
Source dataset
uspto-grants-1983_07
Patent number
US04391627

Reaction notes

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