Water → HCID 13922868, compound

HRID 979567Notes

Reaction equation

HRID 979567 reaction equation
CO[CH2:3][C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1.B(Br)(Br)[Br:18].O>C(Cl)Cl>[Br:18][CH2:3][C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 13922867HCID 13922867, compound

Product 1

HCID 13922868HCID 13922868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a suspension of 5-methoxymethyl-2sulfamoylbenzo[b]thiophene (7.4 g, 0.029 mol) in 300 ml of dry methylene chloride cooled to -30° C. was added boron tribromide (30 ml of a lM solution in methylene chloride, 0.03 mol) over a 20 minute period. The resulting solution was stirred for 11/2 hours as the temperature rose to ambient. The solution was cooled to 0° C. and there was added dropwise 150 ml of water keeping the temperature below 20° C. The methylene chloride layer was separated and the aqueous suspension was extracted with three portions (200 ml) of methanol-chloroform (50/50). The combined extracts were washed with ice water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 8.8 g of tan solid (quantitative yield of crude product) which after recrystallization from 1,2-dichloroethane had m.p. 171°-173° C.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe methylene chloride layer was separated
  3. extractionthe aqueous suspension was extracted with three portions (200 ml) of methanol-chloroform (50/50)
  4. washThe combined extracts were washed with ice water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04bd24ae9b5149cfb049b36bf16771c4
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

Loading…