Sodium Carbonate → N-[2-(4-nitro-2-methylphenylamino)ethyl]-2,2,2-trifluoroacetamide

HRID 970235Notes

Reaction equation

HRID 970235 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].Cl.[F:19][C:20]([F:28])([F:27])[C:21]([NH:23][CH2:24][CH2:25][NH2:26])=[O:22].CN1CCCC1=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:26][CH2:25][CH2:24][NH:23][C:21](=[O:22])[C:20]([F:28])([F:27])[F:19])=[C:3]([CH3:11])[CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 23021610N-(2-aminoethyl)-2,2,2-trifluoroacetamide hydrochloride

Product 1

HCID 23104329N-[2-(4-nitro-2-methylphenylamino)ethyl]-2,2,2-trifluoroacetamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

1.55 g (0.01 mol) of 2-fluoro-5-nitrotoluene, 2.65 g (0.025 mol) of sodium carbonate, 2.11 g (0.011 mol) of 2-(trifluoroacetamido)ethylamine hydrochloride and 10 ml of N-methyl-pyrrolidone were introduced into a three-necked flask under nitrogen. The mixture was heated to 90° C. After reaction for 48 hours, the reaction mixture was cooled and 30 ml of distilled water were then added slowly with vigorous stirring. A yellow precipitate appeared. This precipitate was filtered off, washed several times with water and then with pentane, and dried under vacuum. 1.9 g of expected nitro derivative (1) were obtained in the form of a yellow powder.

Workup

  1. customAfter reaction for 48 hours
  2. temperaturethe reaction mixture was cooled
  3. filtrationThis precipitate was filtered off
  4. washwashed several times with water
  5. dry with materialwith pentane, and dried under vacuum

Sources & evidence

ORD record
ord-30b2ebf634ba4af2924cdcd55c2bb20e
Source dataset
uspto-grants-2007_12
Patent number
US07311737B2

Reaction notes

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