Methyl iodide → 11H-Dibenzo(b,e)(1,4)diazepin-11-one, 5,10-dihydro-10-methyl-

HRID 482233

反応式

HRID 482233 の反応式
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[H-].[Na+].I[CH3:20]>CN(C)C=O>[CH3:20][N:8]1[C:2](=[O:1])[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]1=2

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one

生成物 1

HCID 3604211H-Dibenzo(b,e)(1,4)diazepin-11-one, 5,10-dihydro-10-methyl-収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine (10 g, 0.048 mol, Synthesis, (1985), 550) in dry dimethylformamide (100 ml) kept under an atmosphere of nitrogen, sodium hydride (2.1 g, 0.052 mol, 60% dispersion in oil) was added, and the reaction mixture was stirred for 1.5 h. iodomethane (3.27 ml, 0.052 mol) was slowly added keeping the temperature below 30° C. and the mixture was stirred overnight. The reaction mixture was quenched with saturated ammonium chloride (20 ml) and poured onto ice water (300 ml). The solid was filtered off and washed with plenty of water and dried. This yielded 10.4 g of crude 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine which was recrystallised from methanol (200 ml), to give 6.7 g (63%) of 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine. M.p. 210°-211° C.

後処理

  1. additionwas slowly added
  2. customthe temperature below 30° C.
  3. customThe reaction mixture was quenched with saturated ammonium chloride (20 ml)
  4. additionpoured onto ice water (300 ml)
  5. filtrationThe solid was filtered off
  6. washwashed with plenty of water
  7. customdried
  8. customThis yielded 10.4 g of crude 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine which was recrystallised from methanol (200 ml)

出典と根拠

ORDレコード
ord-da186f2e08fd46a390347aea6d149277
出典データセット
uspto-grants-1998_08
特許番号
US05795888

関連ノート

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