Dichloromethane → N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

HRID 622193ノート

反応式

HRID 622193 の反応式
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[CH3:2].C(N(CC)CC)C.C(Cl)Cl.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>O>[CH2:20]([O:19][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=1)(=[O:40])=[O:39])[CH3:21]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 13911324HCID 13911324、化合物

生成物 1

HCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal収率 97%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

2.18 g (10 mmol) of 2-methoxy-3,4-methylenedioxybenzylamine hydrochloride (1) and 3.06 ml (22 mmol) of triethylamine were added to 30 ml of methylene chloride. Then, 1.91 g (10 mmol) of p-toluene sulfonyl chloride was added portionwise under water-cooling. The resulting mixture was stirred at room temperature for one hour. 20 ml of water was added for liquid separation. The methylene chloride layer was washed with 15 ml of water and dried over anhydrous magnesium sulfate followed by filtration thereof. The solvent was distilled off under vacuum. 30 ml of n-hexane was added to the residue and stirred for 30 minutes. The resulting crystals were collected by filtration, washed with n-hexane and dried to obtain 3.25 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-p-toluenesulfonic amide (2) (yield 97%). It was recrystallized from ethyl acetate, m.p. 150°-151° C. IR and NMR spectra of the resultant product are listed below. ##STR31##

後処理

  1. temperaturecooling
  2. washThe methylene chloride layer was washed with 15 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfollowed by filtration
  5. distillationThe solvent was distilled off under vacuum
  6. addition30 ml of n-hexane was added to the residue
  7. stirringstirred for 30 minutes
  8. filtrationThe resulting crystals were collected by filtration
  9. washwashed with n-hexane
  10. customdried

出典と根拠

ORDレコード
ord-e6f921a4a7514067a144bf2920d37826
出典データセット
uspto-grants-1988_09
特許番号
US04769480

反応ノート

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