Triethylamine → HCID 14479796, compound

HRID 2165856Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:18]([C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])([O-:20])=[O:19]>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH:7][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[N+:18]([O-:20])=[O:19])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

One gram of 3-isopropylaniline and 0.8 gram of triethylamine were dissolved in 50 ml of THF, cooled to 0° C. and agitated. A solution prepared by dissolving 1.37 grams of 2-nitrobenzoyl chloride in 20 ml of THF was dropwisely added. After agitating for 30 minutes, the reaction mixture was filtered and THF in the filtrate was distilled off under reduced pressure. The residue was extracted with benzene, and rinsed with 3N-HCl, a saturated sodium bicarbonate solution and water successively in this order. The benzene layer was dried by adding anhydrous magnesium sulfate and then benzene was distilled off under reduced pressure to obtain the desired product. The yield was 1.79 grams (85%), and the product had a melting point of 65.5° to 68.5° C. and an IR absorption peak at 1660 cm-1 (c=0).

Workup

customA solution prepared
additionwas dropwisely added
stirringAfter agitating for 30 minutes
filtrationthe reaction mixture was filtered
distillationTHF in the filtrate was distilled off under reduced pressure
extractionThe residue was extracted with benzene
washrinsed with 3N-HCl
dry with materialThe benzene layer was dried
additionby adding anhydrous magnesium sulfate
distillationbenzene was distilled off under reduced pressure

Sources & evidence

ORD record: ord-cdba7f1cecbf4f4788427b7974bd49cb
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04942178

Reaction notes

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