4-Chlorobenzenesulfonyl chloride → HCID 14181184, compound

HRID 1608049Notes

Reaction equation

HRID 1608049 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([O:13][CH2:14][C:15]([NH2:17])=[O:16])[CH:6]=[CH:5][C:4]1=2.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>O1CCCC1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:1][CH2:2][CH:3]2[CH2:12][CH2:11][CH2:10][C:9]3[CH:8]=[C:7]([O:13][CH2:14][C:15]([NH2:17])=[O:16])[CH:6]=[CH:5][C:4]2=3)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14181183HCID 14181183, compound

Product 1

HCID 14181184HCID 14181184, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 mol of 5-aminomethyl-5,6,7,8-tetrahydro-naphth-2-yl-oxyacetamide (Example 7), 0.11 mol of 4-chlorobenzenesulphonyl chloride and 0.11 mol of triethylamine are stirred in 200 ml of tetrahydrofuran at room temperature for 3 hours. The mixture is filtered, the filtrate is evaporated, the residue is taken up in CH2Cl2 and the mixture is washed with 1N HCl, saturated NaHCO3, 1N HCl and saturated NaCl solution, dried over Na2SO4 and evaporated. The residue is purified by flash chromatography over silica gel using CH2Cl2MeOH 5:1.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. washthe mixture is washed with 1N HCl, saturated NaHCO3, 1N HCl and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue is purified by flash chromatography over silica gel using CH2Cl2MeOH 5:1

Sources & evidence

ORD record
ord-e996a3489ab24100b180ba4ad6daf18a
Source dataset
uspto-grants-1989_09
Patent number
US04868332

Reaction notes

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