Hydrochloric Acid → HCID 70392841, compound

HRID 1383019Notes

Reaction equation

HRID 1383019 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]=[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(OC(=O)C)(=O)C>[CH3:1][N:2]([CH3:19])[CH:3]=[N:4][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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 53723521HCID 53723521, compound

Product 1

HCID 70392841HCID 70392841, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of N,N-dimethyl-N'-[6-methyl-5-oxido-furo[3,2-c]pyridine-2-sulfonyl]formamidine (4.24 g, 15 mmol) (from Example 13, Step B) in acetic anhydride (13 mL), under a nitrogen atmosphere was heated at 140° C. for 20 minutes to give an amber solution. This reaction mixture was cooled to 100° C. and 6% hydrochloric acid (30 mL) was added. After stirring at 100° C. for 4 hours, the reaction mixture was poured into saturated sodium carbonate (~100 mL) carefully. The product was extracted into methylene chloride, dried over anhydrous sodium sulfate, filtered through a charcoal pad and evaporated to dryness. This residue was triturated with diethyl ether/methylene chloride to give the product (2.21 g, 52% yield) which was used as is.

Workup

  1. customto give an amber solution
  2. temperatureThis reaction mixture was cooled to 100° C.
  3. extractionThe product was extracted into methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered through a charcoal pad
  6. customevaporated to dryness
  7. customThis residue was triturated with diethyl ether/methylene chloride

Sources & evidence

ORD record
ord-e114cadce5c64c58b607f8d6f4772297
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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