Carbon Dioxide → Propan-2-yl 2-(methanesulfonyl)hydrazine-1-carboxylate

HRID 596925Notes

Reaction equation

HRID 596925 reaction equation
[NH2:1][NH2:2].C([O-])([O-])=O.[Na+].[Na+].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(=O)=O.Cl[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]>C(#N)C>[CH3:9][S:10]([NH:1][NH:2][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])(=[O:12])=[O:11]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 7917Isopropyl chloroformateHCID 9321HydrazineHCID 10340Sodium Carbonate2×HCID 31297Methanesulfonyl chloride

Product 1

HCID 22752965Propan-2-yl 2-(methanesulfonyl)hydrazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

In a 1-liter 3-neck flask is placed 17 g. (0.5 mole) anhydrous hydrazine, 27 g. (1/4 mole) Na2CO3 and 100 cc. acetonitrile. The mixture is stirred as 57.3 g. (1/2 mole) of methanesulfonyl chloride is added slowly. The temperature of the mixture increases and CO2 is evolved. Then another 27 g. of Na2CO3 is added and the mixture is stirred as 61.5 g. (0.5 mole) of isopropyl chloroformate is added, keeping the temperature under 40° C. Finally the mixture is stirred 2 hours and then cooled to 10° C. and filtered, washed with cold water and dried. This product melts at 129°-131° C.

Workup

  1. customIn a 1-liter 3-neck flask is placed
  2. temperatureThe temperature of the mixture increases
  3. stirringthe mixture is stirred as 61.5 g
  4. customunder 40° C
  5. stirringFinally the mixture is stirred 2 hours
  6. filtrationfiltered
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-61ccc48d8ac942b9a4b961c301a5cb6f
Source dataset
uspto-grants-1977_03
Patent number
US04012432

Reaction notes

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