Pyrrole-2-carboxaldehyde → HCID 6074183, compound

HRID 646182Notes

Reaction equation

HRID 646182 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1>O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](=[CH:6]/[C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)/[C:16]#[N:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 6074183HCID 6074183, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1H-pyrrole-2-carbaldehyde (3.3 g, 34.7 mmol) and 4-chlorophenylacetonitrile (5.5 g, 33.0 mmol, 0.95 equivalents) in water (50 ml) was heated to 50° C. When all the solid material had melted, the vigorously stirred mixture was treated with 40% aqueous Triton B (14 ml, 5.6 mmol). Precipitation began almost immediately. Stirring was continued for 5 h at 50° C., breaking up lumps when necessary. The still warm suspension was filtered through a sintered glass funnel and washed with warm water. The yellow precipitate was dried at the pump (6.63 g). This is Compound 2 in TABLE 8.

Workup

  1. additionthe vigorously stirred mixture was treated with 40% aqueous Triton B (14 ml, 5.6 mmol)
  2. customPrecipitation
  3. filtrationThe still warm suspension was filtered through a sintered glass funnel
  4. washwashed with warm water
  5. customThe yellow precipitate was dried at the pump (6.63 g)

Sources & evidence

ORD record
ord-27a2d0faa97a44aaadd11abf2ec1053a
Source dataset
uspto-grants-2010_04
Patent number
US07705038B2

Reaction notes

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