Hydrochloric Acid → HCID 1039656, compound

HRID 2079500Notes

Reaction equation

HRID 2079500 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[NH2:9].[C:10]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].Cl.N1C=CC=C[CH:26]=1>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:26])[CH:5]=[CH:4][C:3]=1[NH:9][S:20]([C:17]1[CH:18]=[CH:19][C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 701102-Bromo-4-chloroanilineHCID 1398824-t-Butylbenzenesulfonyl chloride

Product 1

HCID 1039656HCID 1039656, compound

Conditions

Temperature
60 °C

Procedure

2-Bromo-4-chloro-phenylamine (2.06 g, 10 mmol) and 4-tert-butylbenzenesulfonyl chloride (2.55 g, 11 mmol) were suspended in anhydrous pyridine (10 mL) and heated at 60° C. for 4 h. After cooling to room temperature the reaction mixture was added to 6 M HCl (100 mL) and the product was extracted with ethyl acetate (3×50 mL). The combined organic extract was dried over MgSO4, the solvent was evaporated, and the crude product was purified by flash chromatography to afford the title compound as a white solid. MS: (M+H)/z=403.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. extractionthe product was extracted with ethyl acetate (3×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. customthe solvent was evaporated
  6. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b72c139212304c8e8e6e83aafcb67a02
Source dataset
uspto-grants-2011_04
Patent number
US07932252B2

Reaction notes

Loading…