2-Chloroethanol → HCID 66954413, compound

HRID 1619115Notes

Reaction equation

HRID 1619115 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:18][CH2:19][CH2:20][OH:21].CS(O)(=O)=O.[C:27](=O)([O-])O.[Na+].Cl[CH2:33][Cl:34]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:12][CH2:13][C:14]([O:21][CH2:20][CH2:19][Cl:18])([O:17][CH2:27][CH2:33][Cl:34])[CH2:15][CH2:16]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 342-ChloroethanolHCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 66953983HCID 66953983, compound

Product 1

HCID 66954413HCID 66954413, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6′-bromospiro[cyclohexane-1,3′-indoline]-2′,4-dione (preparation 21a, 4.0 g, 13.6 mmol), 2-chloroethanol (20 mL), methanesulphonic acid (0.25 mL) and freshly activated molecular sieves (20 g) in dichloromethane (20 mL) and toluene (40 mL) was stirred at ambient temperature for 4 days. Solid sodium hydrogen carbonate was added to neutralize the mixture and the suspension was filtered and the filter cake was washed with several portions of dichloromethane. The filtrate and washings were combined and evaporated and the residue was purified by flash chromatography (200:1 dichloromethane/methanol) to give the title compound (3.9 g, 66%) as a white solid.

Workup

  1. filtrationthe suspension was filtered
  2. washthe filter cake was washed with several portions of dichloromethane
  3. customevaporated
  4. customthe residue was purified by flash chromatography (200:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-ed26572a6b1644c2ae18f0c72c98ade9
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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