Triethylamine → N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide

HRID 502735Notes

Reaction equation

HRID 502735 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH2:29])[CH2:23][CH2:22]1.C(N(CC)CC)C>C(Cl)Cl>[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH:29][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 4082852-MorpholinoethylamineHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 59427894N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-nitro-5-(trifluoromethyl)benzoic acid (300 mg, 1.29 mmol, 1.0 equiv) and thionyl chloride (2.0 ml) was heated at 75° C. for 1 h. The solvent was removed in vacuo and the residue taken up in CH2Cl2 (5.0 ml). To the solution was added 2-morpholinoethanamine (185 mg, 1.42 mmol, 1.1 equiv) and triethylamine (0.54 ml, 3.86 mmol, 3.0 equiv). After the reaction was complete, the solution was diluted with CH2Cl2 (ca. 10 ml) and washed with water and brine. After drying with Na2SO4 and concentration in vacuo, the resulting N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide was advanced without further purification. MS m/z: 348 (M+H+); Calculated for C14H16F3N3O4: 347.1

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with water and brine
  3. dry with materialAfter drying with Na2SO4 and concentration in vacuo
  4. customthe resulting N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide was advanced without further purification

Sources & evidence

ORD record
ord-355fa31aa4ef4b6dba3fbca6b79af093
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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