Phosgene → HCID 20478817, compound

HRID 1649520Notes

Reaction equation

HRID 1649520 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[C:13]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)(=[O:11])=[O:10])=[O:7])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[CH3:26][N:25]([CH3:27])[S:22]([C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:20])([F:19])[F:21])=[CH:17][C:12]=1[S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])(=[O:23])=[O:24]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 12819767HCID 12819767, compound

Product 1

HCID 20478817HCID 20478817, compound

Procedure

A solution of 12.5 g of N'-(butylaminocarbonyl)-N,N-dimethyl-4-(trifluoromethyl)-1,2-benzenedisulfonamide, and 0.1 g of DABCO in 75 ml of mixed xylenes was heated to 136°. To this solution was added 2.2 ml of liquid phosgene over a period of two hours at a rate that the temperature was maintained between 125° and 135°. The temperature was kept at 130° for 1/2 hour after the addition. The solution was cooled and filtered under a nitrogen atmosphere to remove a small amount of insoluble solid then concentrated at 60°-70° in vacuo. The residue of 2-(N,N-dimethylsulfamoyl)-5-(trifluoromethyl)benzenesulfonylisocyanate was an oil weighing 10.4 g and was sufficiently pure for further reaction.

Workup

  1. temperaturewas maintained between 125° and 135°
  2. additionafter the addition
  3. temperatureThe solution was cooled
  4. filtrationfiltered under a nitrogen atmosphere
  5. customto remove a small amount of insoluble solid
  6. concentrationthen concentrated at 60°-70° in vacuo
  7. customwas sufficiently pure for further reaction

Sources & evidence

ORD record
ord-2351ed883e2d4c188c4fe88e097aa27c
Source dataset
uspto-grants-1983_11
Patent number
US04417917

Reaction notes

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