Sodium hydride → HCID 178491032, compound

HRID 2203441Notes

Reaction equation

HRID 2203441 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=3[OH:17])=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].[CH3:20][O:21][C:22]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:23]=1[CH2:24][N:25]([C:38]1[S:42][N:41]=[CH:40][N:39]=1)[S:26]([C:29]1[CH:34]=[C:33]([F:35])[C:32](F)=[CH:31][C:30]=1[F:37])(=[O:28])=[O:27]>CN(C)C=O>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=3[O:17][C:32]3[C:33]([F:35])=[CH:34][C:29]([S:26]([N:25]([CH2:24][C:23]4[CH:43]=[CH:44][C:45]([O:47][CH3:48])=[CH:46][C:22]=4[O:21][CH3:20])[C:38]4[S:42][N:41]=[CH:40][N:39]=4)(=[O:27])=[O:28])=[C:30]([F:37])[CH:31]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 178516061HCID 178516061, compound

Product 1

HCID 178491032HCID 178491032, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenol (0.110 g, 0.45 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (0.020 g of a 60% w/w dispersion in mineral oil, 0.50 mmol) and the reaction mixture was stirred for 1 h at ambient temperature. N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.210 g, 0.47 mmol) was added and the reaction mixture was stirred for 16 h at ambient temperature. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (10 mL). The organic phase was washed with water (2 10 mL) and brine (2 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as an off-white solid in 34% yield (0.102 g): MS (ES+) m/z 669.7 (M+1), 671.7 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 16 h at ambient temperature
  2. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (10 mL)
  3. washThe organic phase was washed with water (2 10 mL) and brine (2 10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with a 0-100% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-553a093141d646a891cccd1dd01a41cc
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

Loading…