Phenylacetyl chloride → HCID 15169592, compound

HRID 1252497Notes

Reaction equation

HRID 1252497 reaction equation
[Na].[CH2:2]([C:4]1[NH:5][C:6](=[O:23])[NH:7][C:8]=1[C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[CH3:21])=[CH:12][CH:11]=1)[CH3:3].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:2]([C:4]1[N:5]([C:31](=[O:32])[CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:6](=[O:23])[N:7]([C:31](=[O:32])[CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]=1[C:9](=[O:22])[C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[CH3:21])=[CH:14][CH:15]=1)[CH3:3].[CH2:2]([C:4]1[NH:5][C:6](=[O:23])[N:7]([C:31](=[O:32])[CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]=1[C:9](=[O:22])[C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[CH3:21])=[CH:14][CH:15]=1)[CH3:3]

Participants

5

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 70040566HCID 70040566, compound

Product 2

HCID 15169592HCID 15169592, compoundHCID 20140112HCID 20140112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 4.2 g (13.2 mmol) of the product of Example I in 35 mL of dimethylformamide is added 3.1 g (19.3 mmol) of phenylacetylchloride in a dropwise fashion. The resulting mixture is stirred at 65° C. under nitrogen for 40 hours. The reaction mixture is cooled and filtered. The filtrate is diluted with 200 ml of ethyl ether and the resulting precipitate is subjected to flash chromatography on silica gel utilizing 5% methanol in methylene chloride as the eluent. The eluates are analyzed utilizing thin layer chromatography and appropriate fractions are combined and evaporated to produce the above referenced products (1) and (2).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. additionThe filtrate is diluted with 200 ml of ethyl ether
  4. customevaporated

Sources & evidence

ORD record
ord-bcaec12ce37344a2a3269a1d5390b586
Source dataset
uspto-grants-1988_05
Patent number
US04743612

Reaction notes

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