Dimethylformamide → HCID 15767485, compound

HRID 1770081Notes

Reaction equation

[NH2:1][C:2]1[N:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22](S(C)(=O)=O)[N:21]=1.[H-].[Na+].CN(C)C=O>O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([NH:1][C:2]2[N:17]=[CH:16][CH:15]=[CH:14][C:3]=2[C:4]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[N:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2.3 g (0.01 mol) of benzyl 2-aminonicotinate, 2.2 g (0.01 mol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.4 g (0.01 mol) of 60% sodium hydride were weighed, and 10 ml of dimethylformamide was added thereto and the mixture was stirred at 100° C. for 2 hours. The mixture was then poured into water, and was extracted with 100 ml of ethyl acetate. The extracted material was then washed with water and a saturated sodium chloride aqueous solution, and was dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was recrystallized with ethanol to obtain 1.6 g of a yellow-brownish powder of the aimed product.

Workup

extractionwas extracted with 100 ml of ethyl acetate
washThe extracted material was then washed with water
dry with materiala saturated sodium chloride aqueous solution, and was dried with anhydrous sodium sulfate
filtrationAfter filtration
distillationthe solvent was distilled off
customthe residue was recrystallized with ethanol

Sources & evidence

ORD record: ord-140b88cc4589484ab0073f339a2025a1
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05385880

Reaction notes

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