Sodium Chloride → 1,5-Bis(methanesulfonyl) carbohydrazide

HRID 839480Notes

Reaction equation

HRID 839480 reaction equation
[NH2:1][NH:2][C:3]([NH:5][NH2:6])=[O:4].C([O-])(O)=O.[Na+].[CH3:12][S:13](Cl)(=[O:15])=[O:14].[Cl-].[Na+]>CO>[CH3:12][S:13]([NH:1][NH:2][C:3]([NH:5][NH:6][S:13]([CH3:12])(=[O:15])=[O:14])=[O:4])(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 73948CarbohydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 867357611,5-Bis(methanesulfonyl) carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 45 g (0.5 mole) carbohydrazide, 84 g NaHCO3 (1.0 mole) and 50 ml methanol was stirred as 114.5 g (1.0 mole) methane sulfonyl chloride was added over 30 minutes. The temperature rose from 25° to 40° C. The stirring was continued for 15 minutes (temp. 44° C). The mixture was then heated to 65° C for two hours, and was then cooled to 25° C and the solid product (including sodium chloride was filtered and washed with methanol and dried. Yield: 146 g. The material was first suspended in water to remove sodium chloride and then filtered, washed with water and dried. Yield: 81 g, m.p. = 207° C dec.

Workup

  1. additionwas added over 30 minutes
  2. customrose from 25° to 40° C
  3. custom(temp. 44° C)
  4. temperaturewas then cooled to 25° C
  5. filtrationwas filtered
  6. washwashed with methanol
  7. customdried
  8. customto remove sodium chloride
  9. filtrationfiltered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-cd517e2214234773a20ebf66baa4af22
Source dataset
uspto-grants-1978_06
Patent number
US04096100

Reaction notes

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