Triethyl phosphite → HCID 13745827, compound

HRID 620723Notes

Reaction equation

BrC[CH2:3][C:4]1[CH:22]=[CH:21][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([O:19][CH3:20])=[O:18])=[O:9])=[CH:6][CH:5]=1.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>>[CH2:25]([O:24][P:23]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([O:19][CH3:20])=[O:18])=[O:9])=[CH:21][CH:22]=1)([O:27][CH2:28][CH3:29])=[O:30])[CH3:26]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 14519649HCID 14519649, compound

Product 1

HCID 13745827HCID 13745827, compound

Procedure

A suspension of 1.07 g of 4-bromoethyl-N-(2-methoxycarbonylphenyl)benzamide in 5 ml of triethyl phosphite was stirred under heating at 140° to 150° C. for 30 minutes. After excess triethyl phosphite had been distilled off in vacuo, the residue was subjected to silica gel column chromatography (eluent; chloroform:methanol=1:1) to give 4-diethoxyphosphinylmethyl-N-(2-methoxycarbonylphenyl)benzamide. It was recrystallized from a benzene-n-hexane mixture to give 1.20 g of colorless needles.

Workup

temperatureunder heating at 140° to 150° C. for 30 minutes
distillationAfter excess triethyl phosphite had been distilled off in vacuo

Sources & evidence

ORD record: ord-9a7d008d315d4268b3409c62368208b3
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822780

Reaction notes

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