Chlorosulfamic acid → HCID 10379871, compound

HRID 327732Notes

Reaction equation

HRID 327732 reaction equation
[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[S:17](Cl)(=[O:20])(=[O:19])[NH2:18]>C(#N)C>[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][S:17](=[O:20])(=[O:19])[NH2:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 10013630HCID 10013630, compound

Product 1

HCID 10379871HCID 10379871, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 9.0 g (0.041 mole) of 3-[4-(1H-imidazol-1-yl)phenoxy]propanol in 150 ml of acetonitrile was treated with a solution of one equivalent of sulfamoyl chloride in 13 ml of acetonitrile. The mixture was stirred for 20 hr. The reaction mixture was concentrated under vacuum and the residue was dissolved in water. The aqueous solution was filtered and the filtrate was basified to pH 8 with potassium carbonate. The mixture was extracted with ethyl acetate. The organic fraction was concentrated under a stream of nitrogen and the precipitate was collected and dried to give 5.2 g (43%) of tan powder, mp 105.0°-106.0° C.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe aqueous solution was filtered
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationThe organic fraction was concentrated under a stream of nitrogen
  6. customthe precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-2451a91bdb9a4c74a6253edafe8d88e7
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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