4-tert-Butylbenzenesulfonamide → N-[4-(hexadecylamino)benzoyl]-4-t-butylbenzenesulfonamide

HRID 1733506Notes

Reaction equation

HRID 1733506 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:28]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>N1C=CC=CC=1>[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:41][S:38]([C:35]2[CH:36]=[CH:37][C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:33][CH:34]=2)(=[O:39])=[O:40])=[O:24])=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 2228724-tert-ButylbenzenesulfonamideHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 20437349N-[4-(hexadecylamino)benzoyl]-4-t-butylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 21.1 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride and 10.8 g. of p-tert-butylbenzenesulfonamide in 250 ml. of pyridine was stirred under reflux for 2 hours and evaporated. The residue was partitioned between 1 N hydrochloric acid and CH2Cl2 and the organic layer was separated, washed with water, dried (MgSO4), and evaporated. Crystallization of the residual glass from CH2Cl2 hexane afforded a white solid, melting point 173°-176° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customevaporated
  3. customThe residue was partitioned between 1 N hydrochloric acid and CH2Cl2
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customCrystallization of the residual glass from CH2Cl2 hexane
  9. customafforded a white solid, melting point 173°-176° C.

Sources & evidence

ORD record
ord-2f3bf2e68c5d454b99c234cab8010ca6
Source dataset
uspto-grants-1980_12
Patent number
US04242273

Reaction notes

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