Methyl chloroformate → HCID 21436031, compound

HRID 2397551Notes

Reaction equation

HRID 2397551 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].O1CCCC1.[CH3:11][C:12]1[NH:24][C:15]2=[N:16][C:17]3[C:22]([N:23]=[C:14]2[N:13]=1)=[CH:21][CH:20]=[CH:19][CH:18]=3>N1C=CC=CC=1>[CH3:5][O:4][C:2]([N:13]1[C:14]2=[N:23][C:22]3[C:17]([N:16]=[C:15]2[N:24]=[C:12]1[CH3:11])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8028Tetrahydrofuran2×HCID 9920560HCID 9920560, compound

Product 1

HCID 21436031HCID 21436031, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6 parts of methyl chloroformate in 50 parts of tetrahydrofuran was added over 30 minutes to a suspension of 4 parts of 2-methyl-1H-imidazo[4,5-b]quinoxaline in 200 parts of tetrahydrofuran and 6 parts of pyridine. The heterogeneous reaction mixture was stirred at 25° for 17 hours. Concentration in vacuo, addition of 200 parts of CH2Cl2, washing with 500 parts of 5% HCl, drying over sodium sulfate, and concentrating in vacuo left a pale yellow solid. Recrystallization from chloroform-hexane gave almost colorless 1-methoxycarbonyl-2-methyl-1H-imidazo[4,5-b]quinoxaline, m.p. 184° (dec.).

Workup

  1. concentrationConcentration
  2. additionin vacuo, addition of 200 parts of CH2Cl2
  3. washwashing with 500 parts of 5% HCl
  4. dry with materialdrying over sodium sulfate
  5. concentrationconcentrating in vacuo
  6. waitleft a pale yellow solid
  7. customRecrystallization from chloroform-hexane

Sources & evidence

ORD record
ord-4e7a963eda0d497dbbcf49ecb7ca105c
Source dataset
uspto-grants-1977_05
Patent number
US04022777

Reaction notes

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