p-Fluoronitrobenzene → HCID 23104820, compound

HRID 33084

Reaction equation

HRID 33084 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][CH2:17][NH2:18].C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:18][CH2:17][CH2:16][C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 116521Thiopheneethanamine

Product 1

HCID 23104820HCID 23104820, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 4-fluoronitrobenzene, 2.16 g of 2-thien-2-ylethanamine, and 2.35 g of K2CO3 were added to a solution of 20 ml of N-methyl-pyrrolidinone. The reaction medium was heated at 60° C. for 12 hours and, after cooling to room temperature, was then poured into a water+ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 3.3 g of N-(4-nitrophenyl)-N-(2-thien-2-ylethyl)amine (1) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe yellow precipitate formed
  3. filtrationwas filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-3f14fcb3e66f45b29749f1fdcc0ca197
Source dataset
uspto-grants-2008_09
Patent number
US07429278B2

Linked notes

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