Phosgene → HCID 13645938, compound

HRID 1380790Notes

Reaction equation

HRID 1380790 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15])(=[O:7])=[O:6].C(N=[C:23]=[O:24])CCC.C(Cl)(Cl)=O>>[CH3:1][O:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]=[C:23]=[O:24])(=[O:16])=[O:15])(=[O:6])=[O:7]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 13645937HCID 13645937, compound

Product 1

HCID 13645938HCID 13645938, compound

Procedure

A mixture of 2-[(2-methoxyethyl)sulfonyl]benzenesulfonamide (9.5 g, 0.034 mol), n-butylisocyanate (4.7 ml, 0.041 mol) and 1,4-diaza[2.2.2]bicyclooctane (0.1 g) in mixed xylenes (58 ml) was heated to 140° with stirring under nitrogen. Liquid phosgene (2.7 ml, 0.039 mol) was added at a rate to maintain an internal temperature between 125°-135°. When the addition was complete, the solution was refluxed for 2 hours, cooled to room temperature under nitrogen purge and then filtered under a nitrogen atmosphere. Removal of solvent in vacuo gave 2-[(2-methoxyethyl)sulfonyl]benzenesulfonyl isocyanate, which was used immediately in Example 5 below, without further purification.

Workup

  1. temperaturewas heated to 140°
  2. temperatureto maintain an internal temperature between 125°-135°
  3. additionWhen the addition
  4. temperaturethe solution was refluxed for 2 hours
  5. custompurge
  6. filtrationfiltered under a nitrogen atmosphere
  7. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-681cff51d4534d21a2d971d5cfbc8982
Source dataset
uspto-grants-1986_04
Patent number
US04584011

Reaction notes

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