4-Chlorophenyl Isocyanate → beta-Oxo-alpha-(4-chlorophenyl carbamoyl)-beta-(2-pyrrolyl)propionitrile

HRID 236347ノート

反応式

HRID 236347 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][C:9]#[N:10])=[O:7].CCN(CC)CC.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>C(COC)OC>[O:7]=[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)[CH:8]([C:26](=[O:27])[NH:25][C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=1)[C:9]#[N:10]

参加物

5

反応物 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 111943553-oxo-3-(1H-pyrrol-2-yl)propanenitrile

生成物 1

HCID 13370090beta-Oxo-alpha-(4-chlorophenyl carbamoyl)-beta-(2-pyrrolyl)propionitrile

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To the solution of 6.7 g of 2-pyrroloylacetonitrile in 25 ml of glyme and 5.5 g of Et3N is added a solution of 8.6 g of 4-chlorophenyl isocyanate in 25 ml of glyme. After the exothermic reaction, the mixture is let stand overnight. Part of the solvent is evaporated and the cooled residue is poured into a solution of 10 ml of 6N HCl in 250 ml of water. After the addition of some methanol, the crude material is collected. It is dissolved in dilute NaOH solution, the solution is treated with charcoal, filtered, and acidified with 6N HCl. The reprecipitated product is collected, washed with water, and triturated with methanol to give solid, m.p. 219°-221°. Recrystallization from methanol gives β-oxo-α-(4-chlorophenyl carbamoyl)-β-(2-pyrrolyl)propionitrile, m.p. 223°-5°.

後処理

  1. customAfter the exothermic reaction
  2. customPart of the solvent is evaporated
  3. additionthe cooled residue is poured into a solution of 10 ml of 6N HCl in 250 ml of water
  4. additionAfter the addition of some methanol
  5. customthe crude material is collected
  6. dissolutionIt is dissolved in dilute NaOH solution
  7. additionthe solution is treated with charcoal
  8. filtrationfiltered
  9. customThe reprecipitated product is collected
  10. washwashed with water
  11. customtriturated with methanol
  12. customto give solid, m.p. 219°-221°
  13. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-6e9d6fb7d44149648f016b9dffb61771
出典データセット
uspto-grants-1987_02
特許番号
US04644010

反応ノート

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