Triethylamine → HCID 22347316, compound

HRID 897911Notes

Reaction equation

HRID 897911 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=S)=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1.S([O-])([O-])(=O)=O.[Cu+2]>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[O:13][C:3]3[CH:4]=[CH:5][C:6]([O:8][C:9]([F:10])([F:11])[F:12])=[CH:7][C:2]=3[N:1]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 161334-Bromophenyl isothiocyanateHCID 27377292-Amino-4-(trifluoromethoxy)phenol

Product 1

HCID 22347316HCID 22347316, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-4-(trifluoromethoxy)phenol (0.9 g, 0.0047 mol) in tetrahydrofuran (60 mL) was added 4-bromophenyl isothiocyanate (1 g, 0.0047 mol) at room temperature. The mixture was stirred for 16 hours at room temperature. Anhydrous copper sulfate (7.1 g, 0.0443 mol, 9.43 eq.), triethylamine (0.67 mL, 0.0047 mol, 1 eq.), and silica gel (8.5 g) were added to the reaction mixture. The mixture was stirred for 4 hours at room temperature. The solvent was removed under reduced pressure. The mixture was filtered through silica gel pad using 25% ethyl acetate/n-heptane as a mobile phase to give orange colored solid. The solid was purified by flash column chromatography on silica using 0%-25% ethyl acetate/n-heptane as a mobile phase. The solvent was removed, and the residue was triturated with n-heptane to give N2-(4-bromophenyl)-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine (0.9 g, 0.0024 mol).

Workup

  1. stirringThe mixture was stirred for 4 hours at room temperature
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe mixture was filtered through silica gel pad
  4. customto give orange colored solid
  5. customThe solid was purified by flash column chromatography on silica using 0%-25% ethyl acetate/n-heptane as a mobile phase
  6. customThe solvent was removed
  7. customthe residue was triturated with n-heptane

Sources & evidence

ORD record
ord-b2432c1308364790999af9f0f9b7243c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…