Chlorosulfonic acid → Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

HRID 370928

反応式

HRID 370928 の反応式
CN=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.ClS(O)(=O)=O.[CH3:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]([O:26][CH3:27])=[O:25].C([O-])(=[O:30])C.[Na+]>O>[CH3:17][N:18]1[C:22]([C:3](=[O:30])[C:4]2[CH:5]=[CH:6][C:7]([CH3:10])=[CH:8][CH:9]=2)=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]([O:26][CH3:27])=[O:25]

参加物

6

反応物 4

HCID 24638Chlorosulfonic acidHCID 103992Methyl 1-methylpyrrol-2-acetateHCID 517045Sodium AcetateHCID 12410496N-Methyl 4-Methylbenzimidoyl Chloride

生成物 1

HCID 118468Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate収率 37%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

N-Methyl 4-methylbenzimidoyl chloride (3.85 g, 23 mmole) was treated with alcohol free chloroform (4.5 ml) and chlorosulfonic acid (0.2 g, 1.7 mmole). Methyl 1-methyl-1H-pyrrole-2-acetate (3.5 g, 23 mmole) was added in one portion, the reaction was fitted with a calcium chloride drying tube and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate. The phases were separated and the organic phase was concentrated under reduced pressure. The residue (6.6 g of a red oil) was dissolved in methanol (50 ml) and treated with sodium acetate (3 g, 36 mmole) and water (10 ml). The reaction was heated at reflux overnight, then cooled in an ice bath. The title compound crystallized and was isolated by filtration, washed with cold methanol, and air dried to yield 2.3 g (37%) of a light tan solid, m.p. 117°-119° C.

後処理

  1. customthe reaction was fitted with a calcium chloride drying tube
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  3. customThe phases were separated
  4. concentrationthe organic phase was concentrated under reduced pressure
  5. dissolutionThe residue (6.6 g of a red oil) was dissolved in methanol (50 ml)
  6. temperatureThe reaction was heated
  7. temperatureat reflux overnight
  8. temperaturecooled in an ice bath
  9. customThe title compound crystallized
  10. customwas isolated by filtration
  11. washwashed with cold methanol, and air
  12. customdried

出典と根拠

ORDレコード
ord-7f234a72010a4c11a9624a66ef33bb94
出典データセット
uspto-grants-1985_07
特許番号
US04528382

関連ノート

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