Thiomorpholine → 2-Nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069269Notes

Reaction equation

HRID 2069269 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:19]2[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589645312-Nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 240 mg (0.90 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester and 0.189 ml (2.00 mmol) of thiomorpholine in 2.5 ml of tetrahydrofuran is heated at reflux for 2 hours. After evaporation of the tetrahydrofuran the residue is distributed between water and ethyl acetate, the organic phase separated and washed with water and brine, dried over Na2SO4 and concentrated yielding 310 mg of 2-nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester as brown powder, m.p. 68-82° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customAfter evaporation of the tetrahydrofuran the residue
  3. customthe organic phase separated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e1371e626af4693b869aedbf39588fa
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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