2-Chloroethanol → HCID 66954413, compound

HRID 2096963Notes

Reaction equation

HRID 2096963 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 10a, 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-44b3b2c69edf494091f1cfe5796bb230
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

Loading…