Phosgene → 2-Nitrophenylmethanesulfonyl isocyanate

HRID 1262961Notes

Reaction equation

HRID 1262961 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11]([NH2:14])(=[O:13])=[O:12])([O-:3])=[O:2].C(N=[C:20]=[O:21])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11]([N:14]=[C:20]=[O:21])(=[O:12])=[O:13])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 13266249(2-Nitrophenyl)methanesulfonamide

Product 1

HCID 132826592-Nitrophenylmethanesulfonyl isocyanate

Procedure

A solution of 9.0 g of the product of Example 3, 4.2 g of butyl isocyanate and 0.1 g of DABCO in 80 ml of dry xylenes was heated to 136°. To this solution was added 3.0 ml of liquid phosgene at such a rate as to maintain the temperature between 125° and 136°. This addition required about 21/2 hours. The solution was cooled to 25°, filtered under nitrogen and stripped in vacuo to give crude 2-nitrophenylmethanesulfonyl isocyanate as a viscous, moisture-sensitive oil showing a sulfonyl isocyanate peak in the infrared at 2230 cm-1.

Workup

  1. temperatureto maintain the temperature between 125° and 136°
  2. additionThis addition
  3. custom2 hours
  4. temperatureThe solution was cooled to 25°
  5. filtrationfiltered under nitrogen

Sources & evidence

ORD record
ord-9acfbe8046b8410489cb01da255f7763
Source dataset
uspto-grants-1984_06
Patent number
US04454334

Reaction notes

Loading…