Hydrochloric Acid → HCID 1098618, compound

HRID 1058199Notes

Reaction equation

HRID 1058199 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([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][CH:7]=[CH:6][C:5]=1[S:10]([NH:27][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7036BenzhydrylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 1098618HCID 1098618, compoundYield 98.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Nitrobenzenesulfonyl chloride (2.50 g) was added to a methylene chloride solution (30 ml) containing benzhydrylamine (1.87 g) and triethylamine (1.58 g) under ice cooling, followed by stirring for 3.3 hours under ice cooling and for 68.7 hours at room temperature. Water (40 ml), 6 N hydrochloric acid (2 ml) and methylene chloride (10 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 dried over sodium sulfate, filtered, concentrated and further dissolved again in ethyl acetate (70 ml), followed by washing with water (20 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and dried under vacuum to obtain N-(2-nitrobenzenesulfonyl)benzhydrylamine (3.71 g; yield: 98.7%).

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. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionfurther dissolved again in ethyl acetate (70 ml)
  8. washby washing with water (20 ml)
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customdried under vacuum

Sources & evidence

ORD record
ord-1b12b97c2e0b4abd87fa6e46093a399f
Source dataset
uspto-grants-2003_02
Patent number
US06515179B2

Reaction notes

Loading…