Dimethylformamide → HCID 10465500, compound

HRID 1509046Notes

Reaction equation

HRID 1509046 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:13]2[N:14]=[CH:15][CH:16]=[N:12]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74824-Nitrobenzyl chlorideHCID 11430Potassium CarbonateHCID 178418936HCID 178418936, compound

Product 1

HCID 10465500HCID 10465500, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 18-mL vial was charged with 1-(chloromethyl)-4-nitro-benzene (500 mg, 3 mmol, 1 eq.), triazole (310 mg, 4.5 mmol, 1.5 eq.), potassium carbonate (1.24 g, 9 mmol, 3 eq.) and DMF (5 ml). After the resulting mixture was stirred at rt overnight, water (20 ml) was added. The precipitate was collected by filtration and washed with small amount of water. After drying, 340 mg of the title compound was obtained as a mixture of two regioisomers (340 mg, 55% yield).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with small amount of water
  3. customAfter drying

Sources & evidence

ORD record
ord-0ab19b1d72034bcfb22a7b67bce599e3
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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