Water → HCID 18414578, compound

HRID 991555Notes

Reaction equation

HRID 991555 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:5]([C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1)=[O:6].[C:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)#[N:23].C(N(CC)CC)C.O>ClCCl>[O:11]1[C:10]2[CH:14]=[CH:15][C:7]([C:5](=[O:6])[CH:4]([NH:3][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:8][C:9]=2[O:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 18414575HCID 18414575, compound

Product 1

HCID 18414578HCID 18414578, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-1-benzo[1,3]dioxol-5-yl-2-pyridin-2-yl-ethanone dihydrochloride (1 g, 3 mmol) was added to a stirring solution of 4-cyano-benzoyl chloride (0.459 g, 3 mmol) in dichloromethane (10 ml). Triethylamine (2 ml, 14 mmol) was added dropwise and the reaction was stirred at ambient temperature for 18 hours. Water was (50 ml) added the organics were extracted into dichloromethane. Chromatographic purification using a dichloromethane solution of ammonia in methanol (0.5% c. ammonia: 4.5% methanol: 95% dichloromethane) yielded the title compound as a pale yellow oil (0.9 g, 76%); m/z (API) 386 (M+H+, 100%).

Workup

  1. additionadded the
  2. extractionorganics were extracted into dichloromethane
  3. customChromatographic purification

Sources & evidence

ORD record
ord-c761d70b620942628dacee40d649e3ca
Source dataset
uspto-grants-2002_10
Patent number
US06465493B1

Reaction notes

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