Ammonium benzoate → HCID 14155061, compound

HRID 1382664Notes

Reaction equation

HRID 1382664 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=1)[N:5]([C:8](=[CH:14]O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=O.C([O-])(=O)C1C=CC=CC=1.[NH4+:31].C1(C)C(C)=CC=CC=1.O>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([N:5]2[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:31]=[CH:6]2)[C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 15830Ammonium benzoateHCID 68147410HCID 68147410, compoundHCID 72727633HCID 72727633, compound

Product 1

HCID 14155061HCID 14155061, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

19.2 g (0.068 mol) of ethyl 2-(3-chloro-6-ethyl-2-methyl-N-formylanilino)-3-hydroxy-acrylate were heated to an internal temperature of 153° C. with 12.3 g (0.088 mol) of ammonium benzoate in 100 ml of xylene with removal of the xylene/water mixture by distillation. The mixture was allowed to cool and was taken up in toluene, and the organic phase was washed twice with 2N sodium hydroxide solution and twice with water, dried over sodium sulfate and evaporated. 15.2 g (85% of theory) of ethyl 1-(3-chloro-6-ethyl-2-methylphenyl)-imidazole-5-carboxylate were obtained as a pale brown oil. Identification was effected by 1H NMR spectroscopy.

Workup

  1. temperatureto cool
  2. washthe organic phase was washed twice with 2N sodium hydroxide solution and twice with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f99e7a3fb069489d97032ab2953d21ef
Source dataset
uspto-grants-1989_02
Patent number
US04808213

Reaction notes

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