Hydrochloric Acid → 2-Benzyloxy-5-acetylbenzenesulfonyl chloride

HRID 565449Notes

Reaction equation

HRID 565449 reaction equation
N[C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.N([O-])=[O:21].[Na+].[S:24]([Cl:27])(Cl)=[O:25]>C(O)(=O)C>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:16](=[O:18])[CH3:17])=[CH:3][C:2]=1[S:24]([Cl:27])(=[O:25])=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 155794401-[3-Amino-4-(benzyloxy)phenyl]ethan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 122327902-Benzyloxy-5-acetylbenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-(3-amino-4-benzyloxyphenyl)ethanone {2.41 g, prepared by the method reported by A. A. Larsen et al in J. Med. Chem., 10, 462-472 (1967)} was dissolved in acetic acid (5 ml) and thereto were added 5 ml of concentrated hydrochloric acid. Thereto was added an aqueopus solution (7 ml) of sodium nitrite (1.0 g) with agitation at −10° C. over a period of 50 minutes. The resulting mixture was agitated for further 28 minutes with ice-cooling, whereupon a solution of thionyl chloride (3.5 ml) in acetic acid (6.5 ml) and an aqueous solution (3 ml) of cupric chloride dihydrate (720 mg) were added thereto succeedingly, followed by agitation for 6 hours while getting the temperature thereof back to room temperature. The deposited precipitate was collected by filtration and dissolved in chloroform and the resulting solution was washed with water and dried, before it was concentrated to a volume of 50 ml under a reduced pressure to prepare a chloroform solution of 2-benzyloxy-5-acetyl-benzenesulfonyl chloride.

Workup

  1. waitsucceedingly, followed by agitation for 6 hours
  2. customback to room temperature
  3. filtrationThe deposited precipitate was collected by filtration
  4. dissolutiondissolved in chloroform
  5. washthe resulting solution was washed with water
  6. customdried, before it
  7. concentrationwas concentrated to a volume of 50 ml under a reduced pressure
  8. customto prepare a chloroform solution of 2-benzyloxy-5-acetyl-benzenesulfonyl chloride

Sources & evidence

ORD record
ord-9b467c585ead4bf8b22712d7e1116e1a
Source dataset
uspto-grants-2001_01
Patent number
US06172099B2

Reaction notes

Loading…