Hydrazine → HCID 6917603, compound

HRID 2410904Notes

Reaction equation

HRID 2410904 reaction equation
[NH2:1][C:2](=S)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:9][NH2:10].O.O=[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:14]=O>C(O)C>[C:16]1([C:13]2[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:9]=[N:10][CH:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 2733398Ethyl thiooxamateHCID 12215922Glyoxal, phenyl-, hydrate

Product 1

HCID 6917603HCID 6917603, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 500 mL three-neck round bottom flask, ethyl 2-amino-2-thioxoacetate (2.5 g, 18.77 mmol) was mixed with ethanol (25 mL). To this orange solution was added via addition funnel a solution of hydrazine (0.590 mL, 18.77 mmol) in Ethanol (15 mL) over 5 minutes. The reaction mixture was stirred for 1 hr. 2-oxo-2-phenylacetaldehyde hydrate (2.86 g, 18.77 mmol) was added to the above mixture and the mixture was stirred overnight at r.t. under N2. The mixture was concentrated and diluted with 10 ml CH2Cl2 and purified by BIOTAGE® with 0-20% EtOAc in CH2Cl2. The fractions containing the product were concentrated to give 2.52 g titled product. MS (ESI) m/z 229.95 (M+H)+. 1H NMR (DMSO-d6) δ ppm 9.82 (s, 1H), 8.30 (d, 2H, J=8.6), 7.7-7.6 (m, 3H), 4.65 (q, 2H, J=7.1), 1.55 (t, 3H, J=7.1).

Workup

  1. stirringthe mixture was stirred overnight at r.t. under N2
  2. concentrationThe mixture was concentrated
  3. additiondiluted with 10 ml CH2Cl2
  4. custompurified by BIOTAGE® with 0-20% EtOAc in CH2Cl2
  5. additionThe fractions containing the product
  6. concentrationwere concentrated

Sources & evidence

ORD record
ord-ede595063ffa4bbdaec94628f311b018
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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