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Sodium hydride → 6-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester

HRID 488744
Notes
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Reaction equation

HRID 488744 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.[H-].[Na+].[C:30]([O:37][CH2:38][CH3:39])(=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C=O)C>[CH2:38]([O:37][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:13]12[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=1)[NH:11][C:10](=[O:27])[N:9]2[C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31265Ethyl hexanoateHCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

Product 1

HCID 697862196-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (500 mg) (1.25 mmol) in DMF (20 ml) was carefully dropped on a suspension of NaH 60% (65 mg) (1.3 eq) in DMF (10 ml) at RT. The reaction mixture was stirred 1 h at RT, then ethyl hexanoate (0.27 ml) (1.2 eq) was added. After 3 h, 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 purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8) to give 6-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester (200 mg) as an oil. 1H NMR (CDCl3): 7.55 (2H, d), 7.25 (2H, d), 7.1 (1H, m), 6.75 (2H, m), 4.95 (1H, m), 4.15 (2H, q), 3.7 (1H, m), 3.1 (1H, m), 3.0 (2H, s), 2.35 (2H, m), 2.2-1.3 (12H, m), 1.23 (3H, t).

Workup

  1. waitAfter 3 h
  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 purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8)

Sources & evidence

ORD record
ord-648cb88e6eb14f0eb49bfd10be449dc3
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06974815B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes