Acetic Anhydride → HCID 10410970, compound

HRID 488739Notes

Reaction equation

HRID 488739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[CH:14][CH2:15][CH2:16][CH2:17][C:12]3([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[NH:11][C:10]2=[O:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([N:11]1[C:12]2([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=3)[CH2:17][CH2:16][CH2:15][CH:14]=[C:13]2[N:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:10]1=[O:27])(=[O:30])[CH3:29]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

Product 1

HCID 10410970HCID 10410970, compound

Procedure

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (150 mg) (0.38 mmol) in acetic anhydride (5 ml) was refluxed 3 days. After cooling, the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (DCM/acetone, 97.5/2.5), then HPLC to give 4-[3-Acetyl-1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (13.5 mg) as a white solid. 1H NMR (CDCl3): 7.55 (2H, d), 7.3-7.2 (3H, m), 6.70 (2H, m), 4.95 (1H, m), 3.70 (1H, d), 3.05 (1H, m), 2.50 (3H, s), 2.45-2.1 (2H, m), 2.1-1.6 (3H, m).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured on water
  3. extractionextracted with tBuOMe
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel (DCM/acetone, 97.5/2.5)

Sources & evidence

ORD record
ord-d5b53e5c8dce47ffba6fa94fc319d6b4
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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