Hydrazine hydrate (1:1) → 6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine

HRID 2039686노트

반응식

HRID 2039686 반응식
[CH3:1][C:2]1[C:3](/[C:7](=[N:14]\[O:15][CH2:16][C:17]2[N:22]=[C:21]([N:23]3C(=O)C4C(=CC=CC=4)C3=O)[CH:20]=[CH:19][CH:18]=2)/[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][S:5][N:6]=1.O.NN>C1COCC1>[CH3:1][C:2]1[C:3](/[C:7](=[N:14]\[O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:4][S:5][N:6]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 873948112-[6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]isoindole-1,3-dione

생성물 1

HCID 873948166-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-{6-[({[(Z)-(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (49 g, 91 mmol) in dry THF (800 mL) was added hydrazine hydrate (22.2 mL, 457 mmol). The reaction mixture was stirred at room temperature for 14 h, then insolubles were removed by filtration and washed with THF. The filtrates were combined and concentrated in vacuo. Purification of the residual oil on silica gel afforded 6-[({[(Z)-(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}oxy)-methyl]pyridin-2-amine as a yellow oil [22.2 g, yield 75%; HPLC/MS: m/z=326 (M+H); log P(HCOOH)=1.54].

후처리

  1. custominsolubles were removed by filtration
  2. washwashed with THF
  3. concentrationconcentrated in vacuo
  4. customPurification of the residual oil on silica gel

출처 및 근거

ORD 기록
ord-f577ca7bc7ec46aaa3f835f6ca2e6433
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

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