Triphenylphosphine → HCID 20285680, compound

HRID 904466Notes

Reaction equation

HRID 904466 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH:18][C:19](=[O:21])[CH3:20])=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=1[CH2:11][Br:12])=[O:5])[CH3:2].[C:22]1([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Br-:12].[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH:18][C:19](=[O:21])[CH3:20])=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=1[CH2:11][P+:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20285671HCID 20285671, compound

Product 1

HCID 20285680HCID 20285680, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

22.2 G. of crude 2,4-diethoxycarbonyl-3-bromomethyl-5-acetylaminothiophene, 19.7 g. (75 mmol) of triphenylphosphine and 700 ml. of toluene were refluxed for 3 hrs. The resulting precipitate was filtered from the hot solution and washed well with toluene to yield (2,4-diethoxycarbonyl-5-acetylamino-3-thenyl)triphenyl phosphonium bromide, m.p. 186°-195° C. The NMR-spectrum showed that the material contained 11% of succinimide.

Workup

  1. filtrationThe resulting precipitate was filtered from the hot solution
  2. washwashed well with toluene

Sources & evidence

ORD record
ord-5d6ab5bf88ad4dc0bcc10aa94a0f3ba4
Source dataset
uspto-grants-1980_10
Patent number
US04230872

Reaction notes

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