Nitric Acid → 5-Chloro-2-ethoxalylamino-3-nitrobenzotrifluoride

HRID 1461258Notes

Reaction equation

HRID 1461258 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]([F:19])([F:18])[F:17])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[C:1]([NH:8][C:9]1[C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]([F:17])([F:18])[F:19])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4550962Ethyl 2-[4-chloro-2-(trifluoromethyl)anilino]-2-oxoacetate

Product 1

HCID 199803055-Chloro-2-ethoxalylamino-3-nitrobenzotrifluoride

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of N-ethoxalyl-4-chloro-2-trifluoromethylaniline in concentrated sulphuric acid (125 ml) was added to a stirred mixture of 100% nitric acid (120 ml) and concentrated sulphuric acid (240 ml). The temperature was kept between 8°-10° C. during the addition. After the addition was completed, the solution was stirred for additionally 20 min. without external cooling, whereafter it was poured onto icewater. This afforded precipitation of the title compound as an oil, which crystallized as light yellow crystals upon standing. The crystals were filtered off and washed extensively with water. M.p. 100°-101° C.

Workup

  1. additionThe temperature was kept between 8°-10° C. during the addition
  2. additionAfter the addition
  3. additionwas poured onto icewater
  4. customThis afforded precipitation of the title compound as an oil, which
  5. customcrystallized as light yellow crystals
  6. filtrationThe crystals were filtered off
  7. washwashed extensively with water

Sources & evidence

ORD record
ord-f721b0078c8f4cfd8a99c63807fa07b5
Source dataset
uspto-grants-1991_12
Patent number
US05075304

Reaction notes

Loading…