Potassium Hydroxide → Ethyl [4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]carbamate

HRID 542466Notes

Reaction equation

HRID 542466 reaction equation
O[N:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](=[O:7])[O:4][CH2:5][CH3:6].[OH-:14].[K+].Cl[C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1>C(O)C>[CH2:5]([O:4][C:3]([NH:2][C:8]1[CH:13]=[CH:12][C:11]([C:20]2[N:21]=[CH:22][C:17](=[O:14])[NH:18][CH:19]=2)=[CH:10][CH:9]=1)=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 73277ChloropyrazineHCID 4418899HCID 4418899, compound

Product 1

HCID 13853581Ethyl [4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]carbamateYield 15.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-hydroxy-N-phenylcarbamate (7.9 g) was added to a solution of potassium hydroxide (2.45 g) in ethanol (125 ml). After the solution had been stirred for 30 minutes, chloropyrazine (5 g) and a small amount of molecular sieve (4 A) pellets were added. The solution was stirred for two hours and allowed to stand for 144 hours to give a dark brown solution. This solution was evaporated under reduced pressure to give an oil which was washed with dilute acetic acid and solidified. This solid was recrystallised from n-propanol, stirred with water for two hours to remove salts, collected and dried to afford the title compound (1.8 g), m.p. 260°-262° C.

Workup

  1. stirringThe solution was stirred for two hours
  2. waitto stand for 144 hours
  3. customto give a dark brown solution
  4. customThis solution was evaporated under reduced pressure
  5. customto give an oil which
  6. washwas washed with dilute acetic acid
  7. customThis solid was recrystallised from n-propanol
  8. stirringstirred with water for two hours
  9. customto remove salts
  10. customcollected
  11. customdried

Sources & evidence

ORD record
ord-5f1c4fae232b485aa3894b6960cbb493
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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