Hydrazine hydrate (1:1) → 2-[(1-benzyl-1H-1,3-benzodiazol-2-yl)sulfanyl]acetohydrazide

HRID 2059959

Reaction equation

HRID 2059959 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][C:19]([O:21]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:25][NH2:26]>C(O)C>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][C:19]([NH:25][NH2:26])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 975431ethyl [(1-benzyl-1H-benzimidazol-2-yl)sulfanyl]acetate

Product 1

HCID 8769682-[(1-benzyl-1H-1,3-benzodiazol-2-yl)sulfanyl]acetohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2-(1-benzyl-1H-benzo[d]imidazol-2-ylthio)acetate 4b (200 mg, 0.61 mmol, 1.0 eq.) in ethanol (5 mL), was added hydrazine monohydrate (61 mg, 1.23 mmol, 2.0 eq.), and the reaction mixture was heated to reflux and stirred at that temperature for 16 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The mixture was dissolved in ethyl acetate (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo giving 4c as a pale yellow solid which was used without further purification (200 mg, 100%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. dissolutionThe mixture was dissolved in ethyl acetate (20 mL)
  5. washwashed with water (20 mL) and brine (20 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc906db936724591ad4b6050577a2ebd
Source dataset
uspto-grants-2012_10
Patent number
US08278327B2

Linked notes

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