2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → HCID 13826855, compound

HRID 542776Notes

Reaction equation

HRID 542776 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][CH:7]=[C:8]([CH:9](Br)Br)[C:4]=2[CH:3]=1.[NH2:14]/[C:15](/[CH3:22])=[CH:16]\[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][CH:7]=[C:8]([CH:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[NH:14][C:15]([CH3:22])=[C:16]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 202072365-Bromo-3-(dibromomethyl)-1-benzothiophene

Product 1

HCID 13826855HCID 13826855, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.35 g of 5-bromo-3-(dibromomethyl)benzo[b]thiophene and 1.6 g of ethyl 3-aminocrotonate in 4 ml of ethanol was heated to reflux for 14 hours. The mixture was evaporated in vacuo and the residue was purified by chromatography over silica gel to provide 0.8 g of the desired title product, m.p. 68°-70° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 hours
  3. customThe mixture was evaporated in vacuo
  4. customthe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-4ea5379d476648cf9fe3e8e432ad3933
Source dataset
uspto-grants-1987_04
Patent number
US04659717

Reaction notes

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