Butyl isocyanate → 2-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide

HRID 279758

Reaction equation

HRID 279758 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16]>C1(C)C(C)=CC=CC=1.N12CCC(CC1)CN2>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:18]([NH:17][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 133646272-(Chloromethyl)benzenesulfonamide

Product 1

HCID 136318872-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamideYield 74.8%

Reagents, catalysts & solvents 2

HCID 136165Diazabicyclo(2.2.2)octaneCatalystHCID 7237O-XyleneSolvent

Procedure

A mixtue of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]-octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with ethyl acetate (75 ml). The aqueous layer was separated, chilled, acidified (pH 4) with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to give 14.6 g of white solid. A sample was recrystallized from toluene to give m.p. 104°-106°.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5.0 hrs
  3. customVolatiles were removed under vacuum
  4. additionthe residue was treated with 0.5N NaOH (200 ml)
  5. extractionextracted with ethyl acetate (75 ml)
  6. customThe aqueous layer was separated
  7. temperaturechilled
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-201b00dd50774394a1d639d4e156cb20
Source dataset
uspto-grants-1986_05
Patent number
US04586952

Linked notes

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