Water → HCID 15599375, compound

HRID 2414130Notes

Reaction equation

HRID 2414130 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:23]=[CH:22][C:10]([CH2:11][S:12][C:13]2[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.O>C(Cl)Cl>[OH:6][C:7]1[CH:23]=[CH:22][C:10]([CH2:11][S:12][C:13]2[S:17][C:16]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 15599374HCID 15599374, compound

Product 1

HCID 15599375HCID 15599375, compoundYield 2.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (3.12 ml, 8.27g, 0.033 mol) in methylene chloride (30 ml) was added dropwise to a stirred solution of 5-(4-methoxybenzylthio)thiophene-2-sulfonamide (3.4 g, 0.11 mol) in methylene chloride (100 ml). The dark reaction mixture was stirred four hours, treated with water (125 ml) and extracted with ethyl acetate (500 ml). The organic layer was separated, washed with water (2×100 ml), saturated NaCl solution (100 ml) and dried (Na2SO4). The filtrate was evaporated to dryness, the residue slurried with ether and filtered to give 0.95 g off-white solid. Recrystallization from dichloroethane gave material with m.p., 167°-168.5° C.

Workup

  1. customThe dark reaction mixture
  2. extractionextracted with ethyl acetate (500 ml)
  3. customThe organic layer was separated
  4. washwashed with water (2×100 ml), saturated NaCl solution (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe filtrate was evaporated to dryness
  7. filtrationthe residue slurried with ether and filtered

Sources & evidence

ORD record
ord-1ed09157060042648f77e4aa6619b108
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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