Hydrazine hydrate (1:1) → HCID 178527914, compound

HRID 1471874Notes

Reaction equation

HRID 1471874 reaction equation
[S:1]1CS[C:2]1=[C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O.O.[NH2:21][NH2:22]>C(O)C>[C:8]1([C:6]2[C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:2]([SH:1])[NH:22][N:21]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86657577HCID 86657577, compound

Product 1

HCID 178527914HCID 178527914, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(1,3-dithietan-2-ylidene)-1,2-diphenylethanone (1.88 g, 6.61 mmol) in ethanol (50 mL) was added hydrazine hydrate (0.496 g, 9.92 mmol). The reaction was refluxed for 16 h, cooled to room temperature and concentrated. The residue was neutralized with HCl (1.0 M) to pH 6-7 and extracted with EtOAc/H2O. The organic extract was dried over MgSO4 and concentrated to give the title compound (1.5 g). LCMS m/z=253.4 [M+H]+, 1H NMR (400 MHz, CDCl3) δ ppm 4.01-4.19 (m, 1H), 6.92-7.58 (m, 10H).

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. concentrationconcentrated
  3. extractionextracted with EtOAc/H2O
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c825b172fb164f178554476e4cae248d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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