Phenyl chloroformate → Phenyl 5-phenylpyrazin-2-ylcarbamate

HRID 2298953Notes

Reaction equation

HRID 2298953 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[N:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][N:13]=1>N1C=CC=CC=1.CCOC(C)=O>[C:18]1([C:15]2[N:16]=[CH:17][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:13][CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 5987342-Amino-5-phenylpyrazine

Product 1

HCID 9879110Phenyl 5-phenylpyrazin-2-ylcarbamateYield 63%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl chloroformate (0.64 mL, 5.1 mmol) was added to a vigorously stirred solution of 2-amino-5-phenylpyrazine 1-1 (794 mg, 4.64 mmol) in pyridine (10 mL) at room temperature. After being stirred at room temperature overnight, the mixture was diluted with EtOAc to give a suspension, in which the desired compound precipitated out. The suspension was successively washed with 1 N KHSO4, brine and dist. water. The precipitate was collected by filtration and dried to give phenyl N-(5-phenyl-2-pyrazinyl)carbamate 1-2 (847 mg, 63%). The filtrate was concentrated under reduced pressure to produce precipitate, which was collected and dried to give the second crop (340 mg, 25%).

Workup

  1. customto give a suspension
  2. customin which the desired compound precipitated out
  3. washThe suspension was successively washed with 1 N KHSO4, brine and dist
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-269f64200c674d578d7aded364d85dc1
Source dataset
uspto-grants-2002_12
Patent number
US06495559B2

Reaction notes

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