Triethylamine → N-[4-Chloro-3-(trifluoromethyl)phenyl]-N′-[(3-nitrophenyl)methyl]urea

HRID 1809156Notes

Reaction equation

HRID 1809156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].Cl.[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23])([O-:18])=[O:17].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([N+:16]([O-:18])=[O:17])[CH:20]=2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 59708553N-[4-Chloro-3-(trifluoromethyl)phenyl]-N′-[(3-nitrophenyl)methyl]ureaYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask was added 4-chloro-3-(trifluoromethyl)-phenyl isocyanate (443 mg, 2.0 mmol, 1.0 eq.) and acetonitrile (3.0 mL). The solution was cooled to 0° C. before a mixture of 3-nitrobenzylamine HCl (377 mg, 2.0 mmol, 1.0 eq.), DMP (1.0 mL), and triethyl amine (0.27 mL, 2.0 mmol, 1.0 eq.) was added dropwise. The reaction was then allowed to warm to RT slowly, and then stirred for an additional 2 h. The reaction was then concentrated to remove acetonitrile. EtOAc and water were added, and the mixture was extracted, washed with brine, dried with Na2SO4, and concentrated to give an oil. Upon sitting at RT, the oil crystallized to give urea 26 (728 mg, 97% yield). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 374.1 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 9.23 (br. s, 1H), 8.14 (m, 1H), 8.09 (m, 1H), 8.04 (d, 1H), 7.74 (d, 1H), 7.62 (m, 2H), 7.52 (d, 1H), 7.04 (br t, 1H), 4.40 (s, 2H) ppm.

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction was then concentrated
  3. customto remove acetonitrile
  4. additionEtOAc and water were added
  5. extractionthe mixture was extracted
  6. washwashed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated
  9. customto give an oil
  10. customUpon sitting at RT
  11. customthe oil crystallized

Sources & evidence

ORD record
ord-5023a4d28ff44b639090cbfbc164dd0d
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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