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Ethanethiol → 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide

HRID 1608202
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인쇄 미리보기

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HRID 1608202 반응식
[H-].[Na+].C(S)C.[NH2:6][C:7]1[C:29]([Cl:30])=[CH:28][C:10]([C:11]([NH:13][CH2:14][CH:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]2)=[O:12])=[C:9]([O:31]C)[CH:8]=1>CN(C)C=O>[NH2:6][C:7]1[C:29]([Cl:30])=[CH:28][C:10]([C:11]([NH:13][CH2:14][CH:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]2)=[O:12])=[C:9]([OH:31])[CH:8]=1
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참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 1972374-amino-N-((4-benzyl-2-morpholinyl)methyl)-5-chloro-2-methoxybenzamide

생성물 1

HCID 148819784-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide수율 70.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
25 °C

실험 절차

To a stirred suspension of 60% sodium hydride (0.52 g) in dimethylformamide (20 ml) is added under ice-coolinga solution of ethanethiol (0.81 g) in dimethylformamide (5 ml). After the mixture is stirred at 25° C. for 0.5 hour, 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-methoxybenzamide (3.4 g) is added, and the mixture is stirred at 100° C. for 1 hour. After cooling, the reaction mixture is evaporated under reduced pressure. The residue is diluted with water, washed with chloroform, and neutralized with 10% hydrochloric acid. The precipiate is collected, washed with water, and recrystallized from isopropyl alcohol to give the monohydrate of the title compound (2.3 g), mp 153°-155° C.

후처리

  1. stirringthe mixture is stirred at 100° C. for 1 hour
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated under reduced pressure
  4. additionThe residue is diluted with water
  5. washwashed with chloroform
  6. customThe precipiate is collected
  7. washwashed with water
  8. customrecrystallized from isopropyl alcohol

출처 및 근거

ORD 기록
ord-fcafa61a702442e7bdd3a3bf7b8ff2a4
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04870074

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