Methyl chloroformate → HCID 10706453, compound

HRID 1637381Notes

Reaction equation

HRID 1637381 reaction equation
[CH3:1][S:2]([N:5]([CH3:11])[NH:6][S:7]([CH3:10])(=[O:9])=[O:8])(=[O:4])=[O:3].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:19]([O:21][CH3:22])=[O:20]>CC(C)=O>[CH3:1][S:2]([N:5]([CH3:11])[N:6]([S:7]([CH3:10])(=[O:8])=[O:9])[C:19]([O:21][CH3:22])=[O:20])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 1306301,2-Bis(methylsulfonyl)-1-methylhydrazine

Product 1

HCID 10706453HCID 10706453, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,2-Bis(methylsulfonyl)-2-(methoxycarbonyl)-1-methylhydrazine (compound 6) was synthesized as follows: A mixture of 1,2-bis(methylsulfonyl)-1-methylhydrazine (Shyam et al., J. Med. Chem. 30 2157-2161 (1987)) (1.00 g, 0.005 mol), anhydrous sodium carbonate (1.9 g, 0.018 mol), methyl chloroformate (1.23 g, 0.013 mol) and acetone (30 ml) was heated under reflux for 18 hr. The reaction mixture was filtered and the filtrate evaporated to dryness in vacuo. The residue, a thick oil, was stirred with methanol (5 ml) and cooled in ice. The solid that separated was filtered and recrystallized from ethanol-petroleum ether (0.63 g, 48.9%). The melting point (Mp) of this compound was found to be approximately 88-89° C. Analysis of the compound by 1H NMR (CDCl3) showed the following results: δ 0 4.0(3H, s, OCH3), 3.5, 3.4, 3.1 (9H, 3s, 2 CH3SO2 and NCH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hr
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated to dryness in vacuo
  5. temperaturecooled in ice
  6. customThe solid that separated
  7. filtrationwas filtered
  8. customrecrystallized from ethanol-petroleum ether (0.63 g, 48.9%)
  9. customto be approximately 88-89° C
  10. customfollowing results

Sources & evidence

ORD record
ord-2a86cc42704c48a1b421e569ac21d672
Source dataset
uspto-grants-2000_03
Patent number
US06040338

Reaction notes

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