1,2-Dichloroethane → Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylate

HRID 1766120Notes

Reaction equation

HRID 1766120 reaction equation
[Si:1]([O:18][CH2:19][C:20](=O)[CH:21](Cl)[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH2:37])=[S:36])=[CH:33][CH:32]=1.ClCCCl.O>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[N:37]=[C:35]([C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:40])([F:29])[F:41])=[CH:39][CH:38]=2)[S:36][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 27348234-(Trifluoromethyl)thiobenzamideHCID 17951839Ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}2-chloro-3-oxobutanoate

Product 1

HCID 17951800Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 ml round-bottom flask equipped with a magnetic stir-bar was mixed ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-chloro-3-oxobutanoate (20.4 g, 52.88 mmoles, 1 eq), 4-trifluoromethylthiobenzamide (12.2 g, 59.5 mmoles, 1.1 eq), 1,2-dichloroethane (150 ml, 0.44M) and H2O (3 ml). This mixture was refluxed for 12 hrs. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3. Once the phases were separated, the organic phase was washed with water, brine and dried over Na2SO4. This was then filtered, concentrated in vacuo and purified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes) to yield 20.3 g (76%) of the titled compound.

Workup

  1. customTo a 500 ml round-bottom flask equipped with a magnetic stir-bar
  2. temperatureThis mixture was refluxed for 12 hrs
  3. washwashed with sat. NaHCO3
  4. customOnce the phases were separated
  5. washthe organic phase was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationThis was then filtered
  8. concentrationconcentrated in vacuo
  9. custompurified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-966e6c49504d4452b1f5147d0fb02aaf
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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