Water → HCID 19733459, compound

HRID 327685Notes

Reaction equation

HRID 327685 reaction equation
[S:1](OCCOC1C=CC(C)=CC=1)(=[O:4])(=[O:3])[NH2:2].[CH3:16][C:17]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])[CH2:18][OH:19].S(Cl)(=O)(=O)N.ClS(N=C=O)(=O)=O.C(N(CC)CC)C.O>C(#N)C>[S:1]([O:19][CH2:18][C:17]([CH3:16])([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:20])(=[O:4])(=[O:3])[NH2:2]

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanateHCID 183516712-Methyl-2-phenoxypropan-1-olHCID 191086962-(4-Methylphenoxy)ethanol sulfamate

Product 1

HCID 19733459HCID 19733459, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared by the procedure used to synthesize 2-(4-methylphenoxy)ethanol sulfamate in Example 33. Thus, 13.2 g (0.0794 mole) of 2-methyl-2-phenoxypropanol was reacted with sulfamoyl chloride prepared from 26.5 ml (0.298 mole) of chlorosulfonyl isocyanate (98%, Aldrich), 33.9 g (0.336 mole) of triethylamine, and 5.3 g (0.294 mole) of water in 250 ml of acetonitrile. The 12.4 g of a viscous, oily residue obtained was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrePAK 500® silica; methylene chloride), then by chromatography (4.5×90 cm glass column; 500 g of silica gel; methylene chloride). Fractions containing title compound were combined and the solvent was evaporated under reduced pressure to give 5.4 g (28%) of a viscous oil.

Workup

  1. customThis compound was prepared by the procedure
  2. customThe 12.4 g of a viscous, oily residue obtained
  3. customwas purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrePAK 500® silica; methylene chloride)
  4. additionFractions containing title compound
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-05b12c5168684373b9d2fb355b548e7c
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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