3-Bromo-4,5-diaminobenzotrifluoride → HCID 23354368, compound

HRID 235303Notes

Reaction equation

HRID 235303 reaction equation
[Br:1][C:2]1[C:3]([NH2:13])=[C:4]([NH2:12])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:14]([O:19]CC)(=S)[C:15]([NH2:17])=O>C(O)CCC>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]2[C:3]=1[N:13]=[C:15]([NH2:17])[C:14](=[O:19])[NH:12]2

Participants

4

Reactant 2

HCID 7357853-Bromo-4,5-diaminobenzotrifluorideHCID 216137632-ethoxy-2-thioxoAcetamide

Product 1

HCID 23354368HCID 23354368, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
25 °C

Procedure

An adaptation of the method of Burrell et al., J. Chem. Soc. Perkin I. 2707 (1973), was used. A mixture of 3-bromo-5-trifluoromethyl-1,2-phenylenediamine (384 mg, 1.50 mmol; Maybridge Co.) and ethyl thiooxamate (220 mg, 1.70 mmol; Aldrich Co.) in 4 mL of 1-butanol was heated to reflux. The resulting solution was stirred under reflux for 6 h. The resulting suspension was cooled to 25 ° C. A pale yellow precipitate appeared. The mixture was vacuum filtered and the solid was washed with EtOH (5×2 mL) and dried in vacuum at 60° C. overnight to yield 125 mg (27.1%) of 5-bromo-7-trifluoromethyl-3-aminoquinoxalin-2(1H)-one (tentatively named as this since the regiochemistry is not sure) as a pale yellow solid of a new compound: mp dec.>267° C. 1H NMR (300 MHz, DMSO-d6) δ 7.680 (s, 1H, H-7), 7.495 (s, 1H, H-5). LRMS: 307 (M+, 100%), 280 (50%).

Workup

  1. temperaturewas heated to reflux
  2. temperatureunder reflux for 6 h
  3. filtrationfiltered
  4. washthe solid was washed with EtOH (5×2 mL)
  5. customdried in vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-e141d4861532484682b95da0738327bd
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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