Hydrochloric Acid → HCID 14372115, compound

HRID 1382998Notes

Reaction equation

HRID 1382998 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[O:16][C:15]2[CH:14]=[C:13]([CH3:17])[N+:12]([O-])=[CH:11][C:10]=2[CH:9]=1)(=[O:7])=[O:6].Cl.C(=O)([O-])[O-:22].[Na+].[Na+].C(OCC)C>C(OC(=O)C)(=O)C>[S:5]([C:8]1[O:16][C:15]2[CH:14]=[C:13]([CH2:17][OH:22])[N:12]=[CH:11][C:10]=2[CH:9]=1)(=[O:7])(=[O:6])[NH2:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 53723521HCID 53723521, compound

Product 1

HCID 14372115HCID 14372115, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N,N-dimethyl-N'-(5-oxido-6-methylfuro[3,2-c]pyridine-2-sulfonyl)formamidine (3.96 g, 14 mmol) in acetic anhydride (12 ml), under a nitrogen atmosphere was heated at 140° C. for 15 minutes to give a dark brown solution. The reaction was cooled to 100° C. and 20% aqueous hydrochloric acid (40 ml) was added and heat was maintained at this temperature for 4 hours. The cooled reaction was carefully made basic with sodium carbonate solution and then exhaustively extracted with ethyl acetate/methanol to isolate product. This extract was dried over sodium sulfate, filtered through a charcoal pad and solvent evaporated to give, after trituration of the residue with diethyl ether, nearly pure product (1.39 g, 43% yield). Recrystallization from hot ethanol afforded pure product (1.14 g), mp 222°-223° C.

Workup

  1. customto give a dark brown solution
  2. temperatureThe reaction was cooled to 100° C.
  3. temperatureheat
  4. temperaturewas maintained at this temperature for 4 hours
  5. customThe cooled reaction
  6. extractionexhaustively extracted with ethyl acetate/methanol
  7. customto isolate product
  8. dry with materialThis extract was dried over sodium sulfate
  9. filtrationfiltered through a charcoal pad and solvent
  10. customevaporated
  11. customto give

Sources & evidence

ORD record
ord-26c31927f5bd45479588a2c07402c232
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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