Water → 1H-Pyrrole, 1-benzoyl-2,5-dihydro-

HRID 612374

Reaction equation

HRID 612374 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:13]/[CH:14]=[CH:15]\[CH2:16]Br.O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([N:9]1[CH2:16][CH:15]=[CH:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2331BenzamideHCID 14797Potassium HydroxideHCID 5354994(Z)-1,4-dibromobut-2-ene

Product 1

HCID 112522831H-Pyrrole, 1-benzoyl-2,5-dihydro-

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

121 g (1 mol) of benzamide in 3 l of toluene are introduced initially, 200 g of powdered potassium hydroxide are introduced with stirring, 32 g (0.1 mol) of tetrabutylammonium bromide are added and the mixture is heated to 40° C. 243 g (1 mol) of 88% cis-1,4-dibromo-2-butene are then added dropwise in such a way that the internal temperature does not exceed 60° C. The mixture is stirred for another 5 hours at 50° C., then poured into water, and the organic phase is separated off, washed with water, dried and concentrated. The residue is distilled under reduced pressure.

Workup

  1. customdoes not exceed 60° C
  2. stirringThe mixture is stirred for another 5 hours at 50° C.
  3. customthe organic phase is separated off
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-cd9b215d99da4c52ba807717bb4107ea
Source dataset
uspto-grants-1999_12
Patent number
US06004956

Linked notes

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