Acetamide, 2-chloro-N-(2,6-dinitrophenyl)- → HCID 20535499, compound

HRID 1156207Notes

Reaction equation

HRID 1156207 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:5]=1[NH:6][C:7](=[O:10])[CH2:8][Cl:9])([O-:3])=[O:2].[CH2:18]([O:21][CH2:22]Cl)[CH2:19][CH3:20]>C(Cl)Cl>[Cl:9][CH2:8][C:7]([N:6]([CH2:22][O:21][CH2:18][CH2:19][CH3:20])[C:5]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=[CH:14][C:4]=1[N+:1]([O-:3])=[O:2])=[O:10]

Participants

4

Reactant 2

HCID 5014604Acetamide, 2-chloro-N-(2,6-dinitrophenyl)-HCID 109644311-(Chloromethoxy)propane

Product 1

HCID 20535499HCID 20535499, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g. of 2',6'dinitro-2-chloroacetanilide, 3.0 ml. of chloromethyl n-propyl ether, 150 ml of methylene chloride and 1.1 gr. of phase transfer catalyst were charged to a round-bottom flask fitted with a mechanical stirrer. To the mixture was added 100 ml. of saturated NA2CO3 in one portion. The resulting mixture was stirred for three-quarter hour at which time GLC showed no starting material indicating the reaction was complete. The product, 2-chloro-2',6'-dinitro-N-(n-propoxymethyl)acetanilide was obtained as a yellow oil, (3.1 g., yield 93%)

Workup

  1. additionof phase transfer catalyst were charged to a round-bottom flask
  2. customfitted with a mechanical stirrer
  3. additionTo the mixture was added 100 ml

Sources & evidence

ORD record
ord-33385e0263664f58b37e2042f1c9477b
Source dataset
uspto-grants-1982_06
Patent number
US04334909

Reaction notes

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