Acetyl chloride → HCID 23504899, compound

HRID 1884820Notes

Reaction equation

HRID 1884820 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[N:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[N:23]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[C:30](Cl)(=[O:32])[CH3:31]>N1C=CC=CC=1.ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([C:12]1[CH:17]=[CH:16][C:15]([S:18](=[O:20])(=[O:19])[NH:21][C:22]2[N:23]=[C:24]([CH3:29])[CH:25]=[C:26]([CH3:28])[N:27]=2)=[CH:14][CH:13]=1)[C:30](=[O:32])[CH3:31]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 13665663HCID 13665663, compound

Product 1

HCID 23504899HCID 23504899, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

18 mg (0.044 mmol) 4-[(1H-benzimidazol-2-ylmethyl)-amino]-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide was dissolved in 2 ml of 15% pyridine in dichloromethane. Acetyl chloride (31 μl, 0.44 mmol) was diluted with 1 ml dichloromethane and solution was added to the reaction mixture. After three hours reaction mixture was washed with acidic water and organic layer was evaporated to dryness. Crystals were purified on silica using gradient elution (chloroform to 5% methanol in chloroform) to obtain white crystals with 30% yield. 1H NMR (DMSO-d6, 500 MHz): 7.97 (2H, m), 7.60 (2H, m), 7.48 (2H, m), 7.14 (2H, m), 6.68 (1H, s), 5.08 (2H, s), 2.18 (6H, s), 1.93 (3H, s); MS (ESI+): m/z 473 (M+Na)+, 451 (M+H)+.

Workup

  1. additionwas added to the reaction mixture
  2. customAfter three hours reaction mixture
  3. washwas washed with acidic water and organic layer
  4. customwas evaporated to dryness
  5. customCrystals were purified on silica using gradient elution (chloroform to 5% methanol in chloroform)
  6. customto obtain white crystals with 30% yield

Sources & evidence

ORD record
ord-f1d1dd2593cb4222bbc62f5023725c38
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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