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

HRID 1042690Notes

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

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

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

Sources & evidence

ORD record: ord-54353f93d0ec4396857d069c8f3baff7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Reaction notes

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