p-Toluidine → N-(4-Methylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 974601Notes

Reaction equation

HRID 974601 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1>O>[CH3:37][C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:11]([N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=3)[CH2:8]2)=[O:12])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053435N-(4-Methylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 1.88 g (0.0067 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1 g (0.007 mole) of potassium carbonate was added 20 ml of tetrahydrofuran and 0.75 g (0.007 mole) of 4-toluidine. After stirring for 0.5 hr, ice was added and stirring continued for 18 hr. The reaction mixture was diluted with water and then decanted from an oil residue which separated. Upon standing, this residue solidified and was recrystallized from acetone to yield 1.1 g (47%) of large, white crystals, m.p. 191°-192° C.

Workup

  1. additionice was added
  2. stirringstirring
  3. waitcontinued for 18 hr
  4. customdecanted from an oil residue which
  5. customseparated
  6. customthis residue solidified and was recrystallized from acetone
  7. customto yield 1.1 g (47%) of large, white crystals, m.p. 191°-192° C.

Sources & evidence

ORD record
ord-e2faaf4c6d0947f2b8e8f1c652530a52
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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