Hydrochloric Acid → 3-(Dodecane-1-sulfonylamino)-4-methoxy-N-(3,4-dichloro-phenyl)-benzamide

HRID 1387595

Reaction equation

HRID 1387595 reaction equation
N1C=CC=CC=1.[CH2:7]([S:19](Cl)(=[O:21])=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)=[O:28].Cl>O>[CH2:7]([S:19]([NH:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)=[O:28])(=[O:21])=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 66280Dodecylsulfonyl chlorideHCID 99486273-Amino-4-methoxy-N-(3,4-dichlorophenyl)-benzamide

Product 1

HCID 186263143-(Dodecane-1-sulfonylamino)-4-methoxy-N-(3,4-dichloro-phenyl)-benzamideYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine (5 mL) was added to a mixture of 1-dodecane-sulfonyl chloride (Maybridge) (0.8 g, 3.0 mmol) and 3-amino-4-methoxy-N-(3,4-dichloro-phenyl)-benzamide from Example 4 (0.73 g, 3.0 mmol) and stirred at room temperature. After 5 days the mixture was heated on a steambath for 1.5 hours, allowed to cool, and added to water (150 mL), acidified with 4N HCl, and stirred for an hour. The precipitate was filtered off, rinsed with water then with ethanol and dried to afford the product (1.3 g); m.p. 15-152° C. after recrystallization from ethanol and chromatography on silica gel in CHCl3/EtOAc (9:1).

Workup

  1. temperatureAfter 5 days the mixture was heated on a steambath for 1.5 hours
  2. temperatureto cool
  3. stirringstirred for an hour
  4. filtrationThe precipitate was filtered off
  5. washrinsed with water
  6. dry with materialwith ethanol and dried

Sources & evidence

ORD record
ord-83fc6643bd6247df8b62ee6a8338232d
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Linked notes

Loading…