Phenylacetyl chloride → HCID 14543802, compound

HRID 2118781Notes

Reaction equation

HRID 2118781 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N(C1CNC1)=[N+]=[N-]>ClCCCl.ClC(Cl)C.C(N(CC)CC)C>[C:1]([CH:2]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[C:24](=[O:25])[CH:23]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:5][CH2:6][CH3:7])=[O:4]

Participants

8

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 7732P-AnisidineHCID 70211Ethyl oxoacetateHCID 21197678HCID 21197678, compound

Product 1

HCID 14543802HCID 14543802, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 17 ml of triethylamine and 5.0 g of the imine formed from ethyl glyoxalate and p-anisidine in 100 ml of refluxing 1,2-dichloroethane was added dropwise over 2 hours a solution of 16 ml of freshly distilled phenylacetyl chloride in 50 ml of dichloroethane. After refluxing for three hours the reaction was worked-up as per the 3-azidoazetidine. The crude residue was chromatographed to yield the cis and trans isomers of 4-carboethoxy-1-(p-methoxyphenyl)-3-phenylazetidin-2-one as oils; cis: NMR (CDCl3): δ 7.2 (m, 7H), 6.7 (d, J=9, 2H), 4.7 (s, 2H), 3.6 (s, 3H), 3.6 (q, J=7, 2H), 0.7 (t, J=7, 3H); trans: NMR (CDCl3): 7.3 (m, 7H), 6.8 (d, J=9, 2H), 4.5 (d, J=2, 1H), 4.45 (d, J=2, 1H), 4.1 (q, J =7, 2H), 3.6 (s, 3H), 1.2 (t, J=7, 3H).

Workup

  1. temperatureAfter refluxing for three hours the reaction
  2. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-18e4f78c7d164c9aaad13e4268803a64
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

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