4-Chlorobenzenesulfonyl chloride → HCID 54417527, compound

HRID 1377383Notes

Reaction equation

HRID 1377383 reaction equation
[CH2:1]([OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>C(Cl)Cl>[CH2:1]([O:27][S:42]([C:39]1[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=1)(=[O:44])=[O:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 681711-Hexacosanol

Product 1

HCID 54417527HCID 54417527, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of hexacosanol (250 mgs, 0.654 mmol), triethylamine (125 1, 0.900 mmol) and 4-chlorobenzenesulphonyl chloride (150 mgs, 0.711 mmol) in methylene chloride (30 ml) is stirred at room temperature for 120 h. The reaction mixture is then diluted with methylene chloride (20 ml) and washed with water (2×50 ml). The organic phase is dried over magnesium sulphate, filtered and concentrated to give a crude product. Flash column chromatography on silica gel (10:1 hexane:ethyl acetate) followed by recrystallization from methanol gives n-hexacosanyl-4-chlorobenzenesulphonate (80 mgs, 22%).

Workup

  1. washwashed with water (2×50 ml)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product
  6. customFlash column chromatography on silica gel (10:1 hexane:ethyl acetate) followed by recrystallization from methanol

Sources & evidence

ORD record
ord-11081f1085fe46a4b1a54faa635e9b6f
Source dataset
uspto-grants-1997_09
Patent number
US05665328

Reaction notes

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