Acetyl chloride → HCID 68773737, compound

HRID 1398810Notes

Reaction equation

HRID 1398810 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:14]([CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[C:13]2[C:20]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:21][CH:22]=[CH:23][C:12]=2[N:11]=1.[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:18][CH2:17][CH:16]([OH:19])[CH2:15][N:14]1[C:13]2[C:20]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:21][CH:22]=[CH:23][C:12]=2[N:11]=[C:10]1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 68762907HCID 68762907, compound

Product 1

HCID 68773737HCID 68773737, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]propane-1,2-diol (Reference Example 88; 46.2 mg, 0.109 mmol) in pyridine (0.5 mL) was added acetyl chloride (0.0155 mL, 0.218 mmol) at 0° C. After 5 hr, the mixture was quenched with aqueous sodium hydrogen carbonate, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by NH flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (32.5 mg, 0.0698 mmol, 64%).

Workup

  1. customthe mixture was quenched with aqueous sodium hydrogen carbonate
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by NH flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-5c2dc643411a41b4acb9de5bf2bb91f9
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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