(E)-4-(1H-imidazol-1-yl)-2-butenamine → HCID 178456322, compound

HRID 568491Notes

Reaction equation

HRID 568491 reaction equation
[N:1]1([CH2:6]/[CH:7]=[CH:8]/[CH2:9][NH2:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[IH:11].CS[C:14]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]3[C:21]=2[C:16](=[CH:17][CH:18]=[CH:19]3)[N:15]=1>C(O)C>[IH:11].[N:1]1([CH2:6]/[CH:7]=[CH:8]/[CH2:9][NH:10][C:14]2[C:22]3[CH:23]=[CH:24][CH:25]=[C:20]4[C:21]=3[C:16](=[CH:17][CH:18]=[CH:19]4)[N:15]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 13371079(E)-4-(1H-imidazol-1-yl)-2-butenamineHCID 201506502-Methylthiobenz(cd)indole hydriodide

Product 1

HCID 178456322HCID 178456322, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 5.0 g of (E)-4-(1H-imidazol-1-yl)-2-butenamine, 11.5 g of 2-(methylthio)benz[cd]indole hydroiodide and 400 ml of ethanol was stirred and heated at reflux for 16 hours, then clarified while hot. The filtrate was concentrated to 250 ml, cooled to -10° C. and the resulting solid collected, washed with ethanol, ether and dried at 60° C. in vacuo, giving 9.3 g of the desired product, mp 152°-155° C. (dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. concentrationThe filtrate was concentrated to 250 ml
  4. customthe resulting solid collected
  5. washwashed with ethanol, ether
  6. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-68081b6f88f141f8bbfdbcfad243a3dd
Source dataset
uspto-grants-1988_03
Patent number
US04728663

Reaction notes

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