Dichloromethane → HCID 68642112, compound

HRID 1498949Notes

Reaction equation

HRID 1498949 reaction equation
ClCCl.C[O:5][C:6]([C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[CH3:32])=[N:22][C:21]=1[CH3:33])(OC)[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:32][C:26]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:25]=1[C:23]1[S:24][C:20]([C:6](=[O:5])[CH2:7][O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[C:21]([CH3:33])[N:22]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68642095HCID 68642095, compound

Product 1

HCID 68642112HCID 68642112, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dichloromethane (2 ml), 5-[1,1-dimethoxy-2-(4-methoxybenzyloxy)ethyl]-2-(2,4-dimethylphenyl)-4-methylthiazole (35 mg) prepared in the Step 31-1-3 was added, and trifluoroacetic acid (0.3 ml) and water (0.1 ml) were added thereto. Thereafter, the mixture was stirred at a room temperature for 5 hours. To the reaction solution, a saturated sodium bicarbonate solution was added, and then the resulting mixture was subjected to extraction with chloroform. The extract was washed with a saturated saline solution, and then dried over sodium sulfate and concentrated under a reduced pressure. The residue was purified by thin-layer chromatography (hexane:ethyl acetate=3:1, toluene:ethyl acetate=3:1) to give the title compound (18 mg, 57%).

Workup

  1. additionwas added
  2. extractionthe resulting mixture was subjected to extraction with chloroform
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by thin-layer chromatography (hexane:ethyl acetate=3:1, toluene:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a652ebf9be4649a78b0367df944303af
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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