2-Nitropropane → HCID 23465183, compound

HRID 443726Notes

Reaction equation

[Na].[N+](C(C)C)([O-])=[O:3].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[N:20]=[C:19]([CH3:21])[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:17]2)=[CH:12][CH:11]=1.CN(C)C=O>O>[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[N:20]=[C:19]([CH3:21])[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:17]2)=[CH:12][CH:11]=1)=[O:3]

Participants

Conditions

Temperature: 18 °C

Procedure

4.6 g of sodium are dissolved in 330 ml of absolute alcohol, with stirring and whilst passing a vigorous stream of nitrogen over the mixture. After cooling to 18° C., 23.2 g of 2-nitropropane are added dropwise in the course of 15 minutes and the reaction mixture is stirred for a further one hour at room temperature. 64.8 g of 2-(p-bromomethylphenyl)-4-methyl-5-carboethoxy-2H-1,2,3-triazole are then introduced, 330 ml of dimethylformamide are added and the reaction mixture is stirred for 22 hours at room temperature. The reaction mixture is then discharged into 2 liters of water and the product which has crystallised out is filtered off with suction, dried in vacuo at 50° to 60° C. and recrystallised from 1 liter of hexane with the aid of bleaching earth. This gives 25.8 g of 2-(p-formyl-phenyl)-4-methyl-5-carboethoxy-2H-1,2,3-triazole with a melting point of 97° to 99° C.

Workup

stirringthe reaction mixture is stirred for a further one hour at room temperature
stirringthe reaction mixture is stirred for 22 hours at room temperature
customthe product which has crystallised out
filtrationis filtered off with suction
customdried in vacuo at 50° to 60° C.
customrecrystallised from 1 liter of hexane with the aid

Sources & evidence

ORD record: ord-37351703601340c89565948635829646
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04261855

Reaction notes

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