Glyoxylic acid, monohydrate → HCID 73855624, compound

HRID 2215100Notes

Reaction equation

HRID 2215100 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[S:5][C:6]=1[CH2:7][S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]2.O.[C:31]([OH:35])(=[O:34])[CH:32]=O>CCOC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=2)[S:5][C:6]=1[CH2:7][S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[C:14](=[CH:32][C:31]([OH:35])=[O:34])[CH2:13][CH2:12]2

Participants

4

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 21949461HCID 21949461, compound

Product 1

HCID 73855624HCID 73855624, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 6-[4-methyl-2-(4-trifluoromethylphenyl)thiazol-5-ylmethylsulfanyl]-3,4-dihydro-2H-naphthalen-1-one (2.0 g, 4.6 mmol) in glyoxylic acid monohydrate (2.0 g, 22 mmol), under nitrogen atmosphere, was warmed to 160° C. and stirred for 1 h. The reaction mixture was cooled to room temperature, dissolved in EtOAc (100 mL) and filtered. The filtrate was washed with water (50 mL×3) and brine. The organic phase was dried over magnesium sulfate, concentrated under vacuum, and purified by recrystallization in ethanol to give 1.02 g (45%) of yellow solid. Analyzed for C24H18NO3S2: Calcd: C, 58.89%; H, 3.71%; N, 2.86%; Found: C, 58.715; H, 3.56%; N, 2.77.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water (50 mL×3) and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. custompurified by recrystallization in ethanol

Sources & evidence

ORD record
ord-f1cfadb729034f85b6f889bde5cfedc1
Source dataset
uspto-grants-2006_09
Patent number
US07109222B2

Reaction notes

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