Triethylamine → 2-[(4-Bromophenyl)amino]-5-benzoxazolecarbonitrile

HRID 897907Notes

Reaction equation

HRID 897907 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[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>C(#N)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[O:10][C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[N:1]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 161334-Bromophenyl isothiocyanateHCID 2712583-Amino-4-hydroxybenzonitrile

Product 1

HCID 590352862-[(4-Bromophenyl)amino]-5-benzoxazolecarbonitrileYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-amino-4-hydroxybenzonitrile (1.84 g, 0.0137 mol) in acetonitrile (140 mL) was added 4-bromophenyl isothiocyanate (2.93 g, 0.0137 mol) at room temperature. The mixture was stirred for 16 hours at room temperature. Cuprous chloride (1.36 g, 0.0137 mol) and triethylamine (1.9 mL, 0.0137 mol) were added to the reaction mixture. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure, and the solid was suspended in methanol. The mixture was filtered through celite pad using methanol. The brownish filtrate was left at 4° for three days. The precipitate was filtered and washed with methanol to yield 2-(4-bromoanilino)-1,3-benzoxazole-5-carbonitrile (2.4 g, 0.0076 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 11.1 min. MS: MH: 313

Workup

  1. stirringThe mixture was stirred for 16 hours at room temperature
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe mixture was filtered through celite pad
  4. waitThe brownish filtrate was left at 4° for three days
  5. filtrationThe precipitate was filtered
  6. washwashed with methanol

Sources & evidence

ORD record
ord-181030fa77bd4636bc2196f059564732
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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