Hydrochloric Acid → HCID 178434363, compound

HRID 2173035Notes

Reaction equation

HRID 2173035 reaction equation
C1(C(C2C=CC=CC=2)=N/N=C(/[C:12]2[S:13][CH:14]=[CH:15][C:16]=2[NH:17][N:18]=[C:19]([C:26]2C=CC=CC=2)C2C=CC=CC=2)\C)C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>CCO>[CH3:26][C:19]1[C:12]2[S:13][CH:14]=[CH:15][C:16]=2[NH:17][N:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 136611525HCID 136611525, compound

Product 1

HCID 178434363HCID 178434363, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (E)-1-(diphenylmethylene)-2-(1-(3-(2-(diphenylmethylene)hydrazinyl)thiophen-2-yl)ethylidene)hydrazine (12.5 g, 25.07 mmol) in EtOH (75 mL) was added concentrated HCl (40 mL). The reaction mixture was heated at 80° C. for 2 hours, then basified with saturated aqueous NaHCO3 (50 mL) and solid NaHCO3 to pH 8-9. The reaction mixture was extracted with EtOAc (2×250 mL). The organic layers were combined, dried over sodium sulfate, and evaporated. The resulting mixture was purified by silica gel column chromatography, eluting with a gradient of 0-20% dichloromethane and methanol. The pure product fractions were combined and evaporated to give the title compound as a tan solid (2.6 g, 75%). 1H NMR (400 MHz, CDCl3) δ ppm 2.42-2.57 (m, 3H), 6.97 (d, J=5.05 Hz, 1H), 7.40 (d, J=5.31 Hz, 1H), 9.04 (br s, 1H). ESI-MS m/z [M+H]+ calc'd for C6H6N2S, 139. found, 139.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (2×250 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe resulting mixture was purified by silica gel column chromatography
  5. washeluting with a gradient of 0-20% dichloromethane and methanol
  6. customevaporated

Sources & evidence

ORD record
ord-8f2f829c7c3f4599b8e713ea42530262
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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