Semicarbazide hydrochloride → [(Aminocarbonyl)hydrazono](phenyl)acetaldehyde

HRID 1099029

Reaction equation

HRID 1099029 reaction equation
C(O[CH:4]([O:13]CC)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)C.Cl.[NH2:17][NH:18][C:19]([NH2:21])=[O:20]>C(O)C.O>[NH2:21][C:19]([NH:18][N:17]=[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:4]=[O:13])=[O:20]

Participants

4

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 225552,2-Diethoxyacetophenone

Product 1

HCID 54444391[(Aminocarbonyl)hydrazono](phenyl)acetaldehydeYield 59.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,2-diethoxy-1-phenylethanone (6.25 g, 0.0300 mol) and semicarbazide hydrochloride (3.34 g, 0.0300 mol) in ethanol-water (1:1 v/v, 50 mL) was heated at 120° C. for 3 h. The mixture was concentrated under reduced pressure. The residue was treated with methanol, filtered, and washed with methanol to give the desired product (3.40 g, 59.3%). Analytical LCMS: (M+H)+=192.1. 1H-NMR (400 MHz, DMSO-D6): δ 11.03 (s, 1H), 7.97-8.01 (m, 2H), 7.61-7.67 (m, 1H), 7.50-7.56 (m, 2H), 7.34 (b, 1H), 6.54 (b, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was treated with methanol
  3. filtrationfiltered
  4. washwashed with methanol

Sources & evidence

ORD record
ord-7409d8c3718d483e828ad53f4d395c39
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Linked notes

Loading…