Dimethylformamide → HCID 15675560, compound

HRID 1614199Notes

Reaction equation

HRID 1614199 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([OH:25])=O)=O.Cl.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C)C=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][C:14]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:23](=[O:25])[C:18]2[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8870Benzenamine hydrochloride (1:1)HCID 15675566HCID 15675566, compound

Product 1

HCID 15675560HCID 15675560, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-methoxyindol-3-yl)-N-(2-carboxyphenyl)propionamide (4.0 g, 11.8 mmol) in 50 ml of THF at room temperature was added 1,1-carbonyldiimidazole (1.92 g, 11.8 mmol). The reaction mixture stirred for one hour after which aniline hydrochloride (3.06 g, 23.6 mmol) and 25 ml of dimethylformamide were added. The reaction mixture was stirred at reflux under a drying tube for two days, allowed to cool, and concentrated in vacuo to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was washed (water, 1N sodium hydroxide, and brine), dried over anhydrous sodium sulfate, and concentrated in vacuo to dryness. Crystallization of the product from ethyl acetate/trace methanol provided 1.86 g of 2-[2-(5-methoxyindol-3-yl)-ethyl]-3-phenyl-4-(3H)quinazolinone as a white powder: mp 220°-221° C.; EIMS: 395 (M+).

Workup

  1. additionwere added
  2. temperatureat reflux under a drying tube for two days
  3. temperatureto cool
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  6. washThe organic layer was washed (water, 1N sodium hydroxide, and brine)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo to dryness
  9. customCrystallization of the product from ethyl acetate/trace methanol

Sources & evidence

ORD record
ord-f108ba22aee047f0aa2c0db58ea9b0bb
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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