Hydrazine hydrate (1:1) → HCID 68754038, compound

HRID 1519762Notes

Reaction equation

HRID 1519762 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([O:23]C)=O)=[O:14])=[CH:8][CH:7]=1>C(O)C.[Cl-].[Na+].O>[NH:2]([C:21]([C:17]1[S:18][CH:19]=[CH:20][C:16]=1[NH:15][C:13](=[O:14])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][CH:8]=1)=[O:23])[NH2:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 897877HCID 897877, compound

Product 1

HCID 68754038HCID 68754038, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Hydrazine monohydrate (0.825 mL, 17.1 mmol) was added to a solution of methyl 3-(2-(4-methoxyphenyl)acetamido)thiophene-2-carboxylate (3.48 g, 11.4 mmol) in ethanol (40 mL) and the resulting solution was stirred at room temperature for 24 h. The mixture was diluted with brine and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/ethyl acetate, 1/1 to 1/9) to give N-(2-(hydrazine-carbonyl)thiophen-3-yl)-2-(4-methoxyphenyl)acetamide (1.71 g, 5.60 mmol, 49%). Retention time (min)=1.300, method [1], MS(ESI) 306.0 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified on a silica gel column (eluant hexane/ethyl acetate, 1/1 to 1/9)

Sources & evidence

ORD record
ord-a57c2ddcfbf44acba1a75bc018d69dc1
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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