Phenylacetyl chloride → HCID 14306427, compound

HRID 1904944Notes

Reaction equation

HRID 1904944 reaction equation
CN(C)[C:3]([S:5][C:6]1[C:11]2=[N:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15](=[O:16])[N:10]2[CH:9]=[CH:8][CH:7]=1)=[O:4].[C:23]1([CH2:29]C(Cl)=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCCl.[I-].[Zn+2].[I-]>[CH2:29]([C:3]([S:5][C:6]1[C:11]2=[N:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15](=[O:16])[N:10]2[CH:9]=[CH:8][CH:7]=1)=[O:4])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 14306461HCID 14306461, compound

Product 1

HCID 14306427HCID 14306427, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 0.129 g of 9-(dimethylcarbamoyl)thio-3ethoxycarbonyl-4H-pyrido[1,2-a]pyrimidin-4-one Ib-85 in 5 ml of 1,2-dichloroethane are added 65 μl of phenylacetyl chloride and 0.13 g of zinc iodide, and the resultant mixture is refluxed in a nitrogen stream for 45 minutes. After cooling, the reaction mixture is shaken with N-hydrochloric acid and the organic layer is washed with saturated brine in order, dried and concentrated in vacuo. The residue is chromatographed on a column of silica gel, eluting with ethyl acetate, whereby 0.118 g of the titled compound Ie-84 is obtained.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer is washed with saturated brine in order
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-fcefc7c6dd584a1eb134b3e7466d7317
Source dataset
uspto-grants-1989_06
Patent number
US04840953

Reaction notes

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