Water → Phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate

HRID 480059Notes

Reaction equation

HRID 480059 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)=[CH:4][N:3]=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].O>N1C=CC=CC=1>[OH:14][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:1][C:16](=[O:17])[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15891Phenyl chloroformateHCID 226607552-Amino-5-(3-hydroxyphenyl)pyrazine

Product 1

HCID 22660683Phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-(3-hydroxyphenyl)pyrazine (89 mg) in pyridine (10 mL) was added under ice-cooling phenyl chloroformate (63 μL). The mixture was stirred for 1 hour and then poured into water (30 mL) and extracted with ethyl acetate (20 mL×3). The extract was washed with saturated saline solution and then dried over anhydrous Na2SO4. The concentration of the solvent left a crystal residue, which was washed with ethyl ether (10 mL) to give the subject compound (51 mg).

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe extract was washed with saturated saline solution
  3. dry with materialdried over anhydrous Na2SO4
  4. waitThe concentration of the solvent left a crystal residue, which
  5. washwas washed with ethyl ether (10 mL)

Sources & evidence

ORD record
ord-c54baf0c5e9b4c47af587c7bc2e0eeaa
Source dataset
uspto-grants-2003_11
Patent number
US06649624B2

Reaction notes

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