Phosgene → 2-[(Dimethylsulfamoyl)methyl]benzene-1-sulfonyl isocyanate

HRID 434461Notes

Reaction equation

HRID 434461 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14])(=[O:5])=[O:4].C(N=[C:23]=[O:24])CCC.C(Cl)(Cl)=O>C1N2CCN(CC2)C1>[CH3:1][N:2]([CH3:17])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]=[C:23]=[O:24])(=[O:15])=[O:14])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 13178728HCID 13178728, compound

Product 1

HCID 131787292-[(Dimethylsulfamoyl)methyl]benzene-1-sulfonyl isocyanateYield 104.5%

Reagents, catalysts & solvents 1

HCID 9237DabcoCatalyst

Procedure

A solution of 14.0 g of the product of Example 4, 5.0 g of n-butyl isocyanate and 0.1 g of DABCO in 90 ml of mixed xylenes was heated to 136°. To this solution was added 3.6 ml of liquid phosgene over a 2 hour period to maintain the temperature between 125° and 136°. The temperature was kept at 130° for 1/2 hour after the addition. The solution was cooled, and filtered under a nitrogen atmosphere and concentrated at 60°-70° in vacuo to give 16.0 g of crude 2-[(dimethylamino)sulfonylmethyl]benzenesulfonyl isocyanate as a moisture sensitive oil. An infrared peak at 2200 cm-1 confirmed the presence of the --SO2NCO group.

Workup

  1. temperatureto maintain the temperature between 125° and 136°
  2. additionafter the addition
  3. temperatureThe solution was cooled
  4. filtrationfiltered under a nitrogen atmosphere
  5. concentrationconcentrated at 60°-70° in vacuo

Sources & evidence

ORD record
ord-58a9530f0c0a468aab2c342076d87931
Source dataset
uspto-grants-1983_08
Patent number
US04397679

Reaction notes

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