Triethylamine → HCID 22346779, compound

HRID 897914Notes

Reaction equation

HRID 897914 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=S)=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1.S([O-])([O-])(=O)=O.[Cu+2]>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[O:10][C:3]3[CH:4]=[CH:5][C:6]([CH2:8][CH3:9])=[CH:7][C:2]=3[N:1]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 161334-Bromophenyl isothiocyanateHCID 7218852-Amino-4-ethylphenol

Product 1

HCID 22346779HCID 22346779, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-4-ethylphenol (0.89 g, 0.0065 mol) in tetrahydrofuran (80 mL) was added 4-bromophenyl isothiocyanate (1.4 g, 0.0065 mol) at room temperature. The mixture was stirred for 2 hours at room temperature. Anhydrous copper sulfate (6.2 g, 0.039 mol), triethylamine (0.9 mL, 0.0065 mol) and silica gel (11.7 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 brown 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-ethyl-1,3-benzoxazol-2-amine (0.96 g, 0.003 mol). RP-HPLC (Delta Pak C18, 5 μm, 300 A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 10 min, 1 mL/min) Rt 12.1 min. MS: MH+: 318

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 brown 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-25851f6606204dabb69301e945a653db
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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