Phosgene → HCID 13472257, compound

HRID 1789133Notes

Reaction equation

HRID 1789133 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([NH2:13])(=[O:12])=[O:11])[C:4]=2[CH2:3][S:2]1.C(N=[C:19]=[O:20])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([N:13]=[C:19]=[O:20])(=[O:11])=[O:12])[C:4]=2[CH2:3][S:2]1

Participants

6

Reactant 4

HCID 6371Phosgene2×HCID 8110Butyl isocyanateHCID 9237DabcoHCID 13472256HCID 13472256, compound

Product 1

HCID 13472257HCID 13472257, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5.5 g of 1,3-dihydrobenzo[c]thiophene-4-sulfonamide, 2.5 g of butyl isocyanate and 0.05 g of DABCO® in 50 ml of xylene was heated to 135° and 2.2 ml of liquid phosgene was added in small portions at approximately 135°. When the addition of phosgene was complete, heating was continued for 5 minutes before the dark brown suspension was cooled to ambient temperature under a slow stream of nitrogen. The reaction mixture was filtered under nitrogen and the filtrate was concentrated in vacuo to give 1,3-dihydrobenzo[c]thiophene-4-sulfonyl isocyanate as a dark red-brown oil. The crude sulfonyl isocyanates was dissolved in methylene chloride (total volume=26 ml) for reaction with aminoheterocycles.

Workup

  1. temperaturewas heated to 135°
  2. temperatureheating
  3. filtrationThe reaction mixture was filtered under nitrogen
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e1893475f31044b7b7638714ac2306e2
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

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