Hydrazine, dihydrochloride → HCID 67171392, compound

HRID 1409372Notes

Reaction equation

HRID 1409372 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13](=O)/[CH:14]=[C:15](\[O-])/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].Cl.Cl.[NH2:26][NH2:27]>C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:27][N:26]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 86714641HCID 86714641, compound

Product 1

HCID 67171392HCID 67171392, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Lithium (Z)-4-(1-benzyl-1H-imidazol-4-yl)-1-ethoxy-1,4-dioxobut-2-en-2-olate (9.80 mmol, 3.0 g) was suspended in dry ethanol (20 ml). Hydrazine dihydro-chloride (12.74 mmol, 1.337 g) was added and the resulting mixture was refluxed for 2 h. The mixture was cooled to ambient temperature and evaporated. The sticky oil was purified by trituration from ethanol. The precipitate was separated by filtration and flushed with cold ethanol. 2.614 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.31 (t, 3H), 4.33 (q, 2H), 5.81 (bs, 2H), 7.11-7.39 (m, 6H), 8.16 (bs, 1H), 9.31 (bs, 1H), 14.50 (bs, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customevaporated
  3. customThe sticky oil was purified by trituration from ethanol
  4. customThe precipitate was separated by filtration
  5. customflushed with cold ethanol

Sources & evidence

ORD record
ord-140a10d3f7b143d896ebd566bea0d30f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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