Hydrochloric Acid → HCID 14372132, compound

HRID 1382992Notes

Reaction equation

HRID 1382992 reaction equation
[S:1]([C:5]1[O:13][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([Cl:14])[C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19].C(=O)([O-])[O-].[Na+].[Na+].[ClH:27]>O.CO.C(O)C.C(OCC)C>[ClH:14].[ClH:27].[S:1]([C:5]1[O:13][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:19][CH2:18][CH2:17][N:16]([CH3:20])[CH3:15])[C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 14372125HCID 14372125, compound

Product 1

HCID 14372132HCID 14372132, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-sulfamoyl-4-chloro-furo[3,2-c]pyridine (1.02 g, 4.4 mmol) in 2-(dimethylamino)ethylamine (1.4 ml, 12.8 mmol) was warmed at 90° C. for 8 hours. The cooled mixture was diluted with water and made basic with saturated sodium carbonate. The product was extracted into ethyl acetate/methanol, dried over anhydrous sodium sulfate, and filtered. The solution was evaporated to give crude product. This residue was dissolved in methanol and excess ethanolic HCl was added. After dilution with diethyl ether, the resultant gum was digested in ethanol to give a powder (0.86 g, 55% yield), mp: 275°-278° C. Recrystallization of this salt by dissolution in a minimum amount of warm water and subsequent dilution with ethanol gave pure dihyrochloride salt (0.56 g) mp: 281°-283° C.

Workup

  1. extractionThe product was extracted into ethyl acetate/methanol
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solution was evaporated
  5. customto give crude product

Sources & evidence

ORD record
ord-d63da6f3084b4aaebc0c02644a0e5f18
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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