Water → HCID 54368629, compound

HRID 327743Notes

Reaction equation

HRID 327743 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([O:13][CH:14](O)[CH3:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:19](Cl)(=[O:22])(=[O:21])[NH2:20].C(N(CC)CC)C.[OH2:31]>C(#N)C>[C:2]1([CH2:1][O:8][C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][O:21][S:19](=[O:22])(=[O:31])[NH2:20])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 19108700HCID 19108700, compound

Product 1

HCID 54368629HCID 54368629, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 30.0 g (0.12 mole) of 4-(benzyloxy)phenoxyethanol in 150 ml of acetonitrile was added simultaneously 59 ml (0.18 mole) of sulfamoyl chloride solution (3.14M solution in acetonitrile) and 19.5 g (0.19 mole) of triethylamine. The resulting clear solution was stirred at ambient temperature for 5 hr and then poured into 2L of water. The resulting solid was collected by filtration and the filter cake was washed with 1.5L of water and dried (air). The solid was recrystallized from chloroform to yield 31.1 g (78%) of a white solid, mp 125°-128° C.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washthe filter cake was washed with 1.5L of water
  3. customdried (air)
  4. customThe solid was recrystallized from chloroform

Sources & evidence

ORD record
ord-ab2076c8e1c043aa949ef8f165051352
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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