Dimethyl Sulfoxide → HCID 66775093, compound

HRID 1644841Notes

Reaction equation

HRID 1644841 reaction equation
[OH-].[K+].CS(C)=O.[NH:7]1[CH:11]=[N:10][N:9]=[N:8]1.Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:22][C:21]=2[S:29]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])=[O:30])=[CH:16][CH:15]=1>O>[CH2:25]([C:23]1[S:22][C:21]([S:29]([NH:32][C:33]([CH3:34])([CH3:35])[CH3:36])(=[O:30])=[O:31])=[C:20]([C:17]2[CH:16]=[CH:15][C:14]([CH2:13][N:8]3[N:9]=[N:10][CH:11]=[N:7]3)=[CH:19][CH:18]=2)[CH:24]=1)[CH:26]([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 66774518HCID 66774518, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 66775093HCID 66775093, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

KOH (112.2 mg, 2.00 mmol, crushed pellets) was added to DMSO (10 mL, dried over 4 A molecular sieve) and stirred for 5 min. Tetrazole (28.0 mg, 0.4 mmol) was added to the mixture, which was then stirred for 2 h. 3-(4-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (130 mg, 0.292 mmol, see step (b) above) was added, the mixture was cooled briefly and stirred for an additional hour before water (50 mL) was added. The reaction mixture was extracted with ethyl acetate (250 mL) and the extract was washed with water (2×50 mL) and brine (0 mL). The organic phase was dried over MgSO4 and the solvent was removed in vacuo. The residue was purified on column chromatography using hexane:acetone (3:1) as eluent to give the sub-title compound (28.6 mg, 0.066 mmol, 23% yield).

Workup

  1. customdried over 4 A molecular sieve) and
  2. stirringwas then stirred for 2 h
  3. temperaturethe mixture was cooled briefly
  4. additionwas added
  5. extractionThe reaction mixture was extracted with ethyl acetate (250 mL)
  6. washthe extract was washed with water (2×50 mL) and brine (0 mL)
  7. dry with materialThe organic phase was dried over MgSO4
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-eff6f7dd76ad4945a5ab8754eaf29a26
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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