4-Toluenesulfonyl chloride → HCID 14548032, compound

HRID 1351026Notes

Reaction equation

HRID 1351026 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>ClCCl>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11164646Hexaethylene Glycol Monobenzyl Ether

Product 1

HCID 14548032HCID 14548032, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred solution of the product of step (a) (1 g) in dichloromethane (20 mL), p -toluenesulfonyl chloride (0.66 g) and triethylamine (0.5 mL) were added and the reaction was stirred at 20° C. for 24 hours. The reaction mixture was diluted with dichloromethane (100 mL) then washed with water (100 mL) and brine (100 mL), dried and the solvent removed in vacuo. Purification by column chromatography on silica gel (Biotage), eluting with 10% ethyl acetate in cyclohexane to give the title compound (1 g). LC retention time 3.37 mins. Mass spectrum m/z 544 [MNH4+]

Workup

  1. washthen washed with water (100 mL) and brine (100 mL)
  2. customdried
  3. customthe solvent removed in vacuo
  4. customPurification by column chromatography on silica gel (Biotage)
  5. washeluting with 10% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-d01f732d0d2c46c491ce729fd4e656a2
Source dataset
uspto-grants-2007_05
Patent number
US07217409B2

Reaction notes

Loading…