Hydrochloric Acid → N-(Diphenylmethyl)-4-nitrobenzenesulfonamide

HRID 1058200Notes

Reaction equation

HRID 1058200 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:14]([NH2:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl.O.C(N(CC)CC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:27][CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7036BenzhydrylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 1380961N-(Diphenylmethyl)-4-nitrobenzenesulfonamideYield 91.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-Nitrobenzenesulfonyl chloride (2.51 g) was added to a methylene chloride solution (30 ml) containing benzhydrylamine (2.12 g) and triethylamine (1.62 g) under ice cooling, followed by stirring for 3 hours under ice cooling and for 69 hours at room temperature. Water (30 ml), 1 N hydrochloric acid (12 ml) and methylene chloride (5 ml) were added to the reaction mixture, followed by extraction and solution separation, and the aqueous layer was extracted again with methylene chloride (10 ml). The resulting extract was concentrated, and ethyl acetate (80 ml) and water (50 ml) were further added, followed by solution separation. The organic layer was washed in turn with saturated aqueous solution of sodium bicarbonate (10 ml) and water (25 ml), and concentrated. The resulting solid was washed with a mixed solution of ether (9 ml)/hexane (20 ml) and successively with hexane (10 ml), and dried under vacuum to obtain N-(4-nitrobenzenesulfonyl)benzhydrylamine (3.81 g; yield: 91.3%).

Workup

  1. extractionfollowed by extraction and solution separation
  2. extractionthe aqueous layer was extracted again with methylene chloride (10 ml)
  3. extractionThe resulting extract
  4. concentrationwas concentrated
  5. additionethyl acetate (80 ml) and water (50 ml) were further added
  6. customfollowed by solution separation
  7. washThe organic layer was washed in turn with saturated aqueous solution of sodium bicarbonate (10 ml) and water (25 ml)
  8. concentrationconcentrated
  9. washThe resulting solid was washed with a mixed solution of ether (9 ml)/hexane (20 ml) and successively with hexane (10 ml)
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1421629eac8840fc865fc1b3160b8eaf
Source dataset
uspto-grants-2003_02
Patent number
US06515179B2

Reaction notes

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