Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 15053524, compound

HRID 2107269Notes

Reaction equation

HRID 2107269 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:12][CH:13]=[C:14]([CH:16]=[CH:17][C:18](OCC)=[O:19])[N:15]=2)=[CH:4][CH:3]=1.BrC1C=CC(NC(=O)NC2SC=C(C=O)N=2)=CC=1.C(OC(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:12][CH:13]=[C:14](/[CH:16]=[CH:17]/[CH2:18][OH:19])[N:15]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 15053523HCID 15053523, compoundHCID 21225700DiisobutylaluminumhydrideHCID 54162137HCID 54162137, compound

Product 1

HCID 15053524HCID 15053524, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Following a procedure similar to that described in Preparation 48, crude ethyl 3-[2-(3-p-bromophenylureido)thiazol-4-yl]acrylate was prepared from 1 g of 2-(3-p-bromophenylureido)thiazole-4-carbaldehyde, 1.2 g of ethoxycarbonylmethylenetriphenylphosphorane and 20 ml of tetrahydrofuran. Subsequently. following a procedure similar to that described in Preparation 49, the desired compound was prepared from 1.1 g of the above crude ethyl ester, 14 ml of a 1M hexane solution of diisobutyl aluminum hydride and 30 ml of tetrahydrofuran. The resulting product was a white powder having the following physical properties.

Workup

  1. customthat described in Preparation 49

Sources & evidence

ORD record
ord-81995949bd0f403fbe3f96551f1b0903
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

Loading…