Acetic Acid → 4'-Hydroxydiazepam

HRID 2083003ノート

反応式

HRID 2083003 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:6]=2[CH:20]=1.C[O-].[Na+].CI.[C:26](O)(=O)C>CN(C)C=O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:26])[C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:6]=2[CH:20]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 870254'-HydroxydesmethyldiazepamHCID 10942334Sodium Methoxide

生成物 1

HCID 1612164'-Hydroxydiazepam収率 6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6.5 g (0.022 mole) of 7-chloro-1,3-dihyro-5-(4-hydroxyphenyl)-2H-1,4-benzodiazepin-2-one in 40 ml of dimethylformamide was added 11.6 ml (0.055 mole) of 4.74 M sodium methoxide in methanol. After 90 min, the mixture was cooled in an ice bath and 9.4 g (0.066 mole) of methyl iodide was added dropwise with stirring. After 18 hr at room temperature the reaction mixture was acidified with acetic acid, and partitioned between 100 ml of dichloromethane and 100 ml of water. The water layer was extracted once more with dichloromethane. The combined dichloromethane extracts were evaporated to dryness. The residual product mixture was separated on a column of Florisil. The column was eluted with dichloromethane, ether and then ethyl acetate. The ethyl acetate fraction was evaporated and crystallized from methanol to give 0.40 g (6%) of product as colorless prisms, mp 225°-259°.

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. custompartitioned between 100 ml of dichloromethane and 100 ml of water
  3. extractionThe water layer was extracted once more with dichloromethane
  4. customThe combined dichloromethane extracts were evaporated to dryness
  5. customThe residual product mixture was separated on a column of Florisil
  6. washThe column was eluted with dichloromethane, ether
  7. customThe ethyl acetate fraction was evaporated
  8. customcrystallized from methanol

出典と根拠

ORDレコード
ord-3642707d311e4284a594ac5724566220
出典データセット
uspto-grants-1978_04
特許番号
US04083948

反応ノート

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