Sodium hydride → HCID 59382247, compound

HRID 425184Notes

Reaction equation

HRID 425184 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]([C:33]([CH3:35])=[CH2:34])=[CH:21][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:39][C:40]([NH:42][CH3:43])=[O:41]>CN(C=O)C.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]([C:33]([CH3:35])=[CH2:34])=[CH:21][C:10]=1[C:11]([N:13]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:39][C:40](=[O:41])[NH:42][CH3:43])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 667732-chloro-N-methylacetamideHCID 66701752HCID 66701752, compound

Product 1

HCID 59382247HCID 59382247, compoundYield 116%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Bis-benzyloxy-N-(4-fluoro-phenyl)-5-isopropenyl-benzamide (0.1 g, 0.21 mmol) [Using method A2 from (2,4-bis-benzyloxy-5-isopropenyl)-benzoic acid (Preparation B5) and 4-fluoro-aniline] was dissolved in DMF (1 ml), treated with 60% NaH in mineral oil (13 mg, 1.5 eq) and stirred at room temperature for 15 min. 2-chloro-N-methyl acetamide (33 mg, 0.12 mmol) was added and the reaction stirred for a further 60 minutes, then diluted with EtOAc and water. The EtOAc layer was separated, washed with brine, dried (MgSO4) and evaporated. The crude material was purified by flash column chromatography eluting with EtOAc to give 75 mg of title compound. MS: [M+H]+ 539.

Workup

  1. stirringthe reaction stirred for a further 60 minutes
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material was purified by flash column chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-da9ea3a22ba742fab2622a152822f504
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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