Water → HCID 53906692, compound

HRID 327691Notes

Reaction equation

HRID 327691 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].O.[S:9]([O:13][CH2:14][CH:15]([OH:26])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])(=[O:12])(=[O:11])[NH2:10].[CH2:27](N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[NH2:5][S:2]([O:26][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH2:14][O:13][S:9](=[O:12])(=[O:11])[NH:10][CH3:27])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962Water2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 19733456HCID 19733456, compound

Product 1

HCID 53906692HCID 53906692, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution (ice-acetone bath) of 14.7 ml (0.166 mole) of chlorosulfonyl isocyanate (98%; Aldrich) in 100 ml of acetonitrile was added dropwise a solution of 2.7 g (0.15 mole) of water in 5 ml of acetonitrile such that the reaction mixture temperature was maintained at ≤7° C. The mixture was stirred vigorously for 10 min, and to it was added a solution of 12.3 g (0.042 mole) of 3-(2-methoxyphenoxy)-1,2-propanediol methyl sulfamate ester (Example 68) and 17.0 g (0.168 mol) of triethylamine in 100 ml of acetonitrile at such a rate that the temperature of the reaction mixture was maintained at ≤12° C. The reaction mixture was stirred vigorously for 3 hr at ambient temperature and treated with 100 ml of water and 200 ml of ethyl acetate. The layers were separated, and the organic layer was washed with 200 ml of water and evaporated under reduced pressure to yield a viscous residue. The residue was partitioned between 200 ml of water and 300 ml of ethyl ether. The organic layer was washed with three 200 ml portions of water (pH neutral to pH paper), dried over magnesium sulfate and the solvent evaporated under reduced pressure to give 8.5 g (55%) of a viscous, oily residue which solidified upon standing. The solid was triturated with 75 ml of methylene chloride, and the precipitate was collected by filtration to yield 4.2 g (27%) of the title compound as a white solid, mp 110°-113° C.

Workup

  1. temperaturewas maintained at ≤7° C
  2. temperaturewas maintained at ≤12° C
  3. stirringThe reaction mixture was stirred vigorously for 3 hr at ambient temperature
  4. customThe layers were separated
  5. washthe organic layer was washed with 200 ml of water
  6. customevaporated under reduced pressure
  7. customto yield a viscous residue
  8. customThe residue was partitioned between 200 ml of water and 300 ml of ethyl ether
  9. washThe organic layer was washed with three 200 ml portions of water (pH neutral to pH paper)
  10. dry with materialdried over magnesium sulfate
  11. customthe solvent evaporated under reduced pressure
  12. customto give 8.5 g (55%) of a viscous, oily residue which
  13. customThe solid was triturated with 75 ml of methylene chloride
  14. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d1d933c57c4f492e8ee67c264a6ee8b2
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

Loading…