1,3-Dichloropropane → N-(2-(3-Chloropropoxy)-4-nitrophenyl)acetamide

HRID 649712Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][CH2:23][CH2:24]Cl>CN(C)C=O>[Cl:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 98.1 g (0.5 mol) of N-(2-hydroxy-4-nitrophenyl)acetamide and 69.2 g (0.5 mol) of potassium carbonate in 500 ml of dimethylformamide was heated to 50° C. with stirring, 113.0 g (1 mol) of 1,3-dichloropropane were then added and heating at 50° C. was continued for 1 hour. The reaction mixture was poured into 4 litres of ice-cold water and the crystalline precipitate was filtered off, reimpasted in water and then in isopropyl alcohol and dried under vacuum at 40° C. over phosphorus pentoxide.

Workup

temperatureheating at 50° C.
filtrationthe crystalline precipitate was filtered off
dry with materialin isopropyl alcohol and dried under vacuum at 40° C. over phosphorus pentoxide

Sources & evidence

ORD record: ord-d48ec152ea0541609e91e762e8766fc7
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06270533B1

Reaction notes

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