4-Toluenesulfonyl chloride → HCID 54036003, compound

HRID 1871939Notes

Reaction equation

HRID 1871939 reaction equation
[O:1]1[C:6]2=[C:7]3[C:11](=[CH:12][CH:13]=[C:5]2[O:4][CH2:3][C@@H:2]1[CH2:14][OH:15])[NH:10][CH:9]=[CH:8]3.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:15][CH2:14][C@H:2]2[O:1][C:6]3=[C:7]4[C:11](=[CH:12][CH:13]=[C:5]3[O:4][CH2:3]2)[NH:10][CH:9]=[CH:8]4)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11138224HCID 11138224, compound

Product 1

HCID 54036003HCID 54036003, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-2,3-dihydro-7H-1,4-dioxino[2,3-e]indol-2-ylmethanol (0.75 g; prepared by the method described above) in dichloromethane (50 ml) was stirred with cooling in an ice bath. 4-(Dimethylamino)pyridine (0.59 g) and 4-toluenesulphonyl chloride (0.84 g) were then added and the solution stirred at ambient temperature overnight. The mixture was diluted with dichloromethane (200 ml), washed sucessively with water (50 ml), saturated aqueous copper(II) sulphate solution (2×50 ml) and water (50 ml), then dried over sodium sulphate and the solvent evaporated to give (S)-2,3-dihydro-7H-1,4-dioxino[2,3-e]indol-2-ylmethyl 4-toluenesulphonate (1.04 g) as a pale brown oil which solidified on standing.

Workup

  1. customprepared by the method
  2. temperaturewith cooling in an ice bath
  3. stirringthe solution stirred at ambient temperature overnight
  4. washwashed sucessively with water (50 ml), saturated aqueous copper(II) sulphate solution (2×50 ml) and water (50 ml)
  5. dry with materialdried over sodium sulphate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-0112228359554c1986396ee1f8974931
Source dataset
uspto-grants-2000_08
Patent number
US06107310

Reaction notes

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