Pyridine → HCID 66621089, compound

HRID 415189Notes

Reaction equation

HRID 415189 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66621373HCID 66621373, compound

Product 1

HCID 66621089HCID 66621089, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-aminophenyl)benzo[d]oxazole-4-carboxamide (150 mg, 0.59 mmol) in dichloromethane (5 mL) was added pyridine (51 mg, 0.65 mmol) and acetyl chloride (49 mg, 0.62 mmol) at 0° C., and the mixture was stirred at room temperature for 4 hr, then the solvent was evaporated under reduced pressure and the residue was re-crystallized in methanol to obtain 2-(4-acetamidophenyl)benzo[d]oxazole-4-carboxamide as a white solid (155 mg, yield 89%). 1H-NMR (400 MHz, DMSO-d6) δ 2.10 (s, 3H), 7.49-7.53 (t, J=8 Hz, 1H), 7.83-7.85 (d, J=8 Hz, 2H), 7.95-7.99 (m, 3H), 8.23-8.26 (d, J=8 Hz, 2H), 8.48 (s, 1H), 10.36 (s, 1H); LC-MS (ESI) m/z 296 [M+1]+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was re-crystallized in methanol

Sources & evidence

ORD record
ord-93f9b624dd3c4390988b1f062356071c
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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