Dicyclohexylcarbodiimide → HCID 178418733, compound

HRID 30898

Reaction equation

HRID 30898 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[C:16]([F:23])[CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[N:1]=2)=[C:16]([F:23])[CH:15]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 27570034-Bromo-2-fluorophenylisothiocyanate

Product 1

HCID 178418733HCID 178418733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55-7.41 (m, 3H), 7.35-7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

Workup

  1. temperatureThe reaction was heated in a 45° C. oil bath overnight
  2. temperaturecooled
  3. concentrationconcentrated at reduced pressure
  4. additionThe dark residue was diluted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting dark brown oil was purified by flash chromatography on silica gel
  9. washeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
  10. customThe title compound was collected as a light pink solid (0.60 g, 57%)

Sources & evidence

ORD record
ord-96df1c5f8f534faaa5ac531f3060bf4f
Source dataset
uspto-grants-2008_09
Patent number
US07423156B2

Linked notes

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