Water → HCID 23025723, compound

HRID 1437482Notes

Reaction equation

HRID 1437482 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=3)[NH2:12])[O:8][C:4]=2[CH:3]=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].O>N1C=CC=CC=1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([NH:12][C:21]([NH:20][CH2:18][CH3:19])=[O:22])[CH:13]=[CH:14][CH:15]=3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 23025926HCID 23025926, compound

Product 1

HCID 23025723HCID 23025723, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(6-bromobenzoxazol-2-yl)aniline (Compound of Example 267) (925 mg) in pyridine (15 ml) was added ethyl isocyanate (680 mg) at room temperature, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with 1 N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain N-[3-(6-bromobenzoxazol-2-yl)phenyl]-N′-ethylurea (986 mg, 86%).

Workup

  1. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  2. washThe organic layer was washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-45966c4773ee4ce68dff0970566a5272
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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