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

HRID 2039686ノート

反応式

HRID 2039686 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-f577ca7bc7ec46aaa3f835f6ca2e6433
出典データセット
uspto-grants-2013_11
特許番号
US08580799B2

反応ノート

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