Hydrazine hydrate (1:1) → (Z)-[(2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydrazine

HRID 70031Notes

Reaction equation

HRID 70031 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:27][NH2:28]>C(Cl)Cl.C(O)C>[N:27](=[C:12](/[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)\[C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:8][CH:9]=1)\[NH2:28]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole

Product 1

HCID 53364199(Z)-[(2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydrazine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1h (230 mg, 0.65 mmol) in 3 mL CH2Cl2 and 3 mL ethanol was added hydrazine hydrate (2 mL). Then the mixture was refluxed for overnight. After completion of the reaction, the residue was absorbed on silica gel and purified by column chromatography to give compounds 2d-cis (80 mg) and 2d-trans (56 mg). NMR (300 MHz, CDCl3) δ 8.01-7.98 (m, 2H), 7.49-7.46 (m, 5H), 7.33 (s, 1H), 6.82 (s, 2H), 3.87 (s, 3H), 3.85 (s, 6H). MS (ESI) m/z 370.1 (M+H)+.

Workup

  1. temperatureThen the mixture was refluxed for overnight
  2. customAfter completion of the reaction
  3. customthe residue was absorbed on silica gel
  4. custompurified by column chromatography
  5. customto give compounds

Sources & evidence

ORD record
ord-aabcac90af5948ec892e22a42c761e4d
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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