4-Methylmorpholine → 4-(Acetylamino)-5-chloro-2-methoxybenzoic acid, 4-(trifluoromethyl)phenylhydrazide

HRID 362463

反応式

HRID 362463 の反応式
C(OC(Cl)=O)C(C)C.[C:9]([NH:12][C:13]1[C:21]([Cl:22])=[CH:20][C:16]([C:17]([OH:19])=O)=[C:15]([O:23][CH3:24])[CH:14]=1)(=[O:11])[CH3:10].CN1CCOCC1.[F:32][C:33]([F:43])([F:42])[C:34]1[CH:39]=[CH:38][C:37]([NH:40][NH2:41])=[CH:36][CH:35]=1>C1COCC1.C(OCC)(=O)C>[F:32][C:33]([F:42])([F:43])[C:34]1[CH:35]=[CH:36][C:37]([N:40]([C:17](=[O:19])[C:16]2[CH:20]=[C:21]([Cl:22])[C:13]([NH:12][C:9](=[O:11])[CH3:10])=[CH:14][C:15]=2[O:23][CH3:24])[NH2:41])=[CH:38][CH:39]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acid

生成物 1

HCID 570124124-(Acetylamino)-5-chloro-2-methoxybenzoic acid, 4-(trifluoromethyl)phenylhydrazide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Iso-butylchloroformate (1.6 ml, 16.4 mmol) was added dropwise to a solution of 4-(acetylamino)-5-chloro-2-methoxybenzoic acid (4 g, 16.4 mmol) and 4-methylmorpholine (1.8 ml, 16.4mmol) in 400 ml of anhydrous THF at 0° C. and stirred for 0.5 h at room temperature before addition of 4-(trifluoromethyl)phenylhydrazine (2.9 g, 16.4 mmol) dissolved in 80 ml of the same solvent. The reaction mixture was stirred 8 h, diluted with ethyl acetate (1 vol), washed with water, saturated NaHCO3 solution, and brine. Concentration gave a solid which was recrystallized from acetonitrile 5.7 g (86%); mp 217°-219° C.; IR(KBr, ν=cm-1) 3410, 3286, 1704, 1670, 1500, 1338, 1238, 1104; 1H NMR (300 MHz, DMSO-d6) δ2.15 (3H, s), 3.88 (3H, s), 6.88 (2H, d, J=8.5 Hz), 7.49 (2H, d, J=8.5 Hz), 7.68 (1H, s), 7.76 (1H, s), 8.61 (1H, br. s), 9.62 (1H, br. s) 10.01 (1H, br. s); MS(ESI)m/z: 400 (M--H-)

後処理

  1. washwashed with water, saturated NaHCO3 solution, and brine
  2. concentrationConcentration
  3. customgave a solid which
  4. customwas recrystallized from acetonitrile 5.7 g (86%)

出典と根拠

ORDレコード
ord-8129a3b1083b4b0d9128fbc03c8ef851
出典データセット
uspto-grants-1999_02
特許番号
US05869509

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