Guanidine Hydrochloride → HCID 9818000、化合物

HRID 399864ノート

反応式

HRID 399864 の反応式
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[CH3:9][S:10]([C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)[CH:22]=1)[C:16](OC)=[O:17])(=[O:12])=[O:11]>CO>[CH3:9][S:10]([C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)[CH:22]=1)[C:16]([N:7]=[C:6]([NH2:8])[NH2:5])=[O:17])(=[O:12])=[O:11]

参加物

5

反応物 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18945432Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

生成物 1

HCID 9818000HCID 9818000、化合物収率 21.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

28% Methanolic sodium methoxide (6.2 ml) was added to a solution of guanidine hydrochloride (3.2 g) in dry methanol (40.0 ml) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate (1.9 g) and the mixture was stirred for 7 hours at the same temperature. The solvent was removed by concentration and the residue was added to a mixture of ethyl acetate, tetrahydrofuran and water. The separated organic layer was washed with brine and dried over magnesium sulfate. The residue was obtained by evaporating a solvent, and purified by column chromatography on alumina eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and diisopropyl ether to give 2-[3-methylsulfonyl-5-(pyrrol-1-yl)benzoyl]guanidine (0.44 g).

後処理

  1. stirringthe mixture was stirred for 7 hours at the same temperature
  2. customThe solvent was removed by concentration
  3. additionthe residue was added to a mixture of ethyl acetate, tetrahydrofuran and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe residue was obtained
  7. customby evaporating a solvent
  8. custompurified by column chromatography on alumina eluting with a mixture of chloroform and methanol (19:1, V/V)
  9. additionThe fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo
  12. customThe residue was recrystallized from a mixture of methanol and diisopropyl ether

出典と根拠

ORDレコード
ord-cb47ea8cb90446498f95effb0ba4a1e0
出典データセット
uspto-grants-1998_10
特許番号
US05824691

反応ノート

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