Water → HCID 86747433, compound

HRID 327784Notes

Reaction equation

HRID 327784 reaction equation
[NH2:1][NH2:2].[F:3][S:4]([F:11])=[C:5](Cl)[C:6]([F:9])([F:8])[F:7].O>CO.CCOCC>[F:3][S:4]([F:11])=[C:5]([NH:1][NH:2][C:5](=[S:4]([F:11])[F:3])[C:6]([F:9])([F:8])[F:7])[C:6]([F:9])([F:8])[F:7]

Participants

6

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 86747434HCID 86747434, compound

Product 1

HCID 86747433HCID 86747433, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydrazine (0.67 g, 0.02 mole) in methanol (5 ml) was stirred in a dry ice-acetone bath while pentafluorothioacetyl chloride (1.8 g, 0.0088 mole) in ether (3 ml) was added dropwise. After 15 minutes at 0° C., the mixture was poured into water and the insoluble material (0.35 g, mp 271° C. dec) was removed. An additional 0.7 g, mp 270° C. dec was recovered by concentrating the ether solution. Total yield of N,N'-bis(pentafluorothioacetyl)hydrazine is 1.05 g (66%); 1H NMR (acetone-d6): 4.78 (pentuplet); IR (KBr): 3190 (NH), 1635 (C=O), 895°-825 (SF5).

Workup

  1. additionwas added dropwise
  2. customthe insoluble material (0.35 g, mp 271° C. dec) was removed
  3. customAn additional 0.7 g, mp 270° C. dec was recovered
  4. concentrationby concentrating the ether solution
  5. custom3190 (NH), 1635 (C=O), 895°

Sources & evidence

ORD record
ord-016a89804acc49bda6b8c5f35d00d2ab
Source dataset
uspto-grants-1993_12
Patent number
US05274103

Reaction notes

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