Dimethyl Disulfide → 1-methylthiomethyl-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

HRID 46520ノート

反応式

HRID 46520 の反応式
C([Li])CCC.[CH3:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12.[CH3:25][S:26]SC>CCCCCC.O1CCCC1>[CH3:25][S:26][CH2:6][C:7]1[C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=12

参加物

6

反応物 3

HCID 12232Dimethyl DisulfideHCID 205556141-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2oneHCID 178418339Butyllithium

生成物 1

HCID 205555951-methylthiomethyl-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

The starting material is prepared as follows: 36.4 ml of 2.5 M n-butyl lithium in hexane are added dropwise under nitrogen and at room temperature to the stirred suspension of 7.8 g of 1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]-azepin-2-one in 70 ml of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 45 minutes and cooled in a dry ice-acetone bath. The solution of 5.45 ml of dimethyl disulfide in 60 ml of tetrahydrofuran is added dropwise and the mixture stirred with said cooling for 2 hours. It is quenched by the slow addition of 150 ml of water, the mixture is extracted with chloroform, the extract is dried and evaporated. The residue is crystallized from diethyl ether and recrystallized from ethyl acetate, to give the 1-methylthiomethyl-3,4,5,5a,6,7-hexahydro9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 182°-184°.

後処理

  1. customThe starting material is prepared
  2. temperaturecooled in a dry ice-acetone bath
  3. stirringthe mixture stirred
  4. temperaturewith said cooling for 2 hours
  5. customIt is quenched by the slow addition of 150 ml of water
  6. extractionthe mixture is extracted with chloroform
  7. customthe extract is dried
  8. customevaporated
  9. customThe residue is crystallized from diethyl ether
  10. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9c3996ee68974fc0a4fa11f5e0daba01
出典データセット
uspto-grants-1979_11
特許番号
US04173633

反応ノート

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