Methanol → HCID 68786209, compound

HRID 2283369Notes

Reaction equation

HRID 2283369 reaction equation
B(Br)(Br)Br.C([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][S:16]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([NH2:29])(=[O:28])=[O:27])(=[O:18])=[O:17])C.CO>ClCCl>[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][S:16]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([NH2:29])(=[O:28])=[O:27])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 68780144HCID 68780144, compound

Product 1

HCID 68786209HCID 68786209, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 M in dichloromethane, 5.4 mL, 5.44 mmol) was added dropwise over 5 min to a suspension of 2-[2-(2-ethoxy-phenyl)-ethenesulfonylamino]-benzenesulfonamide (example 222) (0.21 g, 0.54 mmol) in dichloromethane (10 mL) at −78° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. Cooled to −20° C. and methanol (5 mL) was added slowly. The resulting solution was warmed up to room temperature and heated at 50° C. for 1 hour. The volatiles were removed under reduced pressure and the residue was taken up in methanol (5 mL). The mixture was concentrated in vacuo and the process was repeated once more. The residue was taken up in water (5 mL) and ethyl acetate (15 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave 31 mg (16% yield) of the title compound.

Workup

  1. temperatureCooled to −20° C.
  2. temperatureThe resulting solution was warmed up to room temperature
  3. temperatureheated at 50° C. for 1 hour
  4. customThe volatiles were removed under reduced pressure
  5. concentrationThe mixture was concentrated in vacuo
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-b501865bc70244ad92b02612ce4211ef
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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