(4-Fluoro-2-(trifluoromethyl)phenyl)methanamine → HCID 17819328, compound

HRID 1956714Notes

Reaction equation

HRID 1956714 reaction equation
C(O[C:4]1[C:5](=[O:14])[C:6](=[O:13])[C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])C.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1>C1COCC1>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([F:15])=[CH:17][C:18]=1[C:24]([F:27])([F:25])[F:26])([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 2734878(4-Fluoro-2-(trifluoromethyl)phenyl)methanamineHCID 19082433HCID 19082433, compound

Product 1

HCID 17819328HCID 17819328, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of (0.7 g, 3.55 mmol) of 3-ethoxy-4-(tert-butylamino)-cyclobut-3-ene-1,2-dione and THF (30 mL) was added (0.73 g, 3.78 mmol) of the 4-fluoro-2-trifluoromethylbenzylamine via a syringe. The resulting mixture was stirred at room temperature for 12 hours. After concentration in vacuo, the resulting white solid was recrystallized from hot acetonitrile to give 0.55 gm (52%) of 3-tert-butylamino-4-(4-fluoro-2-trifluoromethyl-benzylamino)-cyclobut-3-ene-1,2-dione as a white solid: mp 192°-194° C.; 1H NMR (DMSO-d6) δ1.36 (s, 9H), 4.88 (d, 2H) 7.67 (m, 5H) ppm; IR (KBr) 3250, 2900, 1800, 1580, 1530 cm-1 ; MS (m/z) 345 ([M+H]+).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe resulting white solid was recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-81d9cbdc76fa4e61997b020c00a123d0
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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