4-Bromophenyl isothiocyanate → N-(4-Bromophenyl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine

HRID 907728Notes

Reaction equation

HRID 907728 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[OH:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC>C(O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[O: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)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 161334-Bromophenyl isothiocyanateHCID 1202462-Amino-4-(trifluoromethyl)phenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9924878N-(4-Bromophenyl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amineYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-(trifluoromethyl)phenol (250 mg, 1.41 mmol) and 1-bromo-4-isothiocyanatobenzene (302 mg, 1.41 mmol) were stirred in ethyl alcohol at ambient temperature for 18 h. The flask was charged with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (405 mg, 2.12 mmol), and the mixture was stirred for 2 h before being heated at reflux overnight The reaction was allowed to cool to rt and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 2 N aqueous hydrochloric acid solution and water, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 85:15 hexanes/ethyl acetate to provide the title compound (315 mg, 62%). LC-MS m/z 357.1 (MH+), retention time 4.20 minutes.

Workup

  1. temperaturebefore being heated
  2. temperatureat reflux overnight The reaction
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2 N aqueous hydrochloric acid solution and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with 85:15 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-94cc5a75f5a74fb98a32da558f8a5fb1
Source dataset
uspto-grants-2011_09
Patent number
US08013166B2

Reaction notes

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