Sodium Acetate → HCID 58088961, compound

HRID 2099224Notes

Reaction equation

HRID 2099224 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:26][CH:27]([C:30]#[N:31])[C:28]#[N:29].C([O-])(=O)C.[Na+]>C(OCC)(OCC)OCC.O>[NH2:29][C:28]1[N:1]([C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=2[CH3:14])[C:5]([NH:7][CH:8]2[CH2:9][CH2:10]2)=[O:6])[CH:15]=[N:26][C:27]=1[C:30]#[N:31]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 563049Aminomalononitrile p-toluenesulphonateHCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 58088961HCID 58088961, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-N-cyclopropyl-4-methyl-benzamide (380 mg, 2.0 mmol) in 2.0 mL of triethyl orthoformate was stirred at 120° C. in microwave for 20 minutes. The solvent was removed under reduced pressure. The residue was dissolved in 5 mL of acetic acid and then was added aminomalononitrile p-toluenesulfonate (506 mg, 2.0 mmol) and sodium acetate (164 mg, 2.0 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with 20 mL of water and the resulting precipitate was filtered to give 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide 3A as a colorless solid (170 mg, 30%). HPLC tR=1.39 min; MS m/z 282 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 5 mL of acetic acid
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-ef704ae30cf442228a3f150a7a020beb
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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