Butyl isocyanate → N-(Butylaminocarbonyl)-2-chloro-6-phenylbenzenesulfonamide

HRID 236231Notes

Reaction equation

HRID 236231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15].[CH2:18]([N:22]=[C:23]=[O:24])[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:18]([NH:22][C:23]([NH:17][S:14]([C:3]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:16])=[O:15])=[O:24])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 138523522-Chloro-6-phenylbenzenesulfonamide

Product 1

HCID 13852353N-(Butylaminocarbonyl)-2-chloro-6-phenylbenzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7.7 g (0.029 mol) 2-chloro-6-phenylbenzenesulfonamide, 3.6 ml (0.032 mol) n-butylisocyanate and 4.1 g (0.03 mol) potassium carbonate was heated in 80 ml dry acetonitrile for 18 hours at reflux. The solvent was evaporated and the residue treated with 1N HCl and ethyl acetate and the insoluble solids were collected, washed with water and then ether. Additional material was obtained from the organic phase of the filtrate to afford a total of 10 g of the title compound, m.p. 184°-186°. NMR (90 MHz, CDCl3), 0.9 (CH3, t, br), 1.4 (4H, m), 3.05 (q, J=7 Hz, 2H), 5.9 (t, br, NH), 7.2-7.6 (m, 8H) ppm.

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated
  3. additionthe residue treated with 1N HCl and ethyl acetate
  4. customthe insoluble solids were collected
  5. washwashed with water
  6. customAdditional material was obtained from the organic phase of the filtrate

Sources & evidence

ORD record
ord-0fe9773b5d3d4222a8064226e90e9782
Source dataset
uspto-grants-1987_02
Patent number
US04643761

Reaction notes

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