Water → HCID 20033724, compound

HRID 231683Notes

Reaction equation

HRID 231683 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[S:16][C:15]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:14][C:13]=2[CH3:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br.O.C(OCC)(=O)C>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[S:16][C:15]([S:17]([NH2:20])(=[O:18])=[O:19])=[CH:14][C:13]=2[CH3:21])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 20033683HCID 20033683, compound

Product 1

HCID 20033724HCID 20033724, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(4-methoxyphenylsulfonyl)-4-methylthiophene-2-sulfonamide (9.75 g, 0.028 mol) was suspended in methylene chloride (150 ml) and a 1.0M solution of boron tribromide in methylene chloride (90 ml, 0.09 mol) was added dropwise over 1/2 hour, at 0° C. Then the solution was stirred at ambient temperature for 5 hours. The solution was added to ice and water (500 ml) and ethyl acetate (500 ml) was added. The organic layer was separated, washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl, dried, filtered and concentrated in vacuo. A yellow oil was obtained which crystallized from ethyl acetate-n-butyl chloride. Yield was 67%. The recrystallized white solid melted at 170°-172° C. Purity and structure were confirmed by C, H, N, analyses, HPLC and NMR.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customA yellow oil was obtained which
  8. customcrystallized from ethyl acetate-n-butyl chloride

Sources & evidence

ORD record
ord-e9112b30181442b3aabf58e92fccc28d
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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