Ethanol → HCID 15104318, compound

HRID 345264Notes

Reaction equation

HRID 345264 reaction equation
N([O-])=O.[Na+].[CH3:5][C:6]1[S:7][C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15](N)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[N:10]=1.C(O)C>O.Cl>[CH3:5][C:6]1[S:7][C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[CH:13]=2)[N:10]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 15104317HCID 15104317, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15104318HCID 15104318, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1.4 g of NaNO2 in 30 ml of water are added dropwise with ice cooling in the course of about 20 minutes to 7 g (0.02 mol) of 2-methyl-5-ethoxycarbonyl-4-(4-amino-3-trifluoromethyl-phenoxy)-thiazole (cf. Example (IV-4) in 40 ml of concentrated hydrochloric acid. After the mixture has been stirred for 5 minutes, 300 ml of ethanol are added, and the mixture is then heated slowly to reflux temperature and refluxed for 30 minutes. The volatile constituents are subsequently removed in vacuo, the oil which remains is then taken up in 50 ml of water, a pH of 8 is established by adding dilute sodium hydroxide solution, the mixture is extracted twice with dichloromethane, the extract is dried (over MgSO4) and evaporated in vacuo, and the crude product which remains is filtered chromatographically through silica gel (eluent: toluene). 5.6 g (83.6 % of theory) of 2-methyl-5-ethoxycarbonyl-4-(3-trifluoromethyl-phenyloxy)-thiazole are obtained; melting point: 56° C.

Workup

  1. temperaturethe mixture is then heated slowly
  2. temperatureto reflux temperature
  3. temperaturerefluxed for 30 minutes
  4. customThe volatile constituents are subsequently removed in vacuo
  5. additionby adding dilute sodium hydroxide solution
  6. extractionthe mixture is extracted twice with dichloromethane
  7. dry with materialthe extract is dried (over MgSO4)
  8. customevaporated in vacuo
  9. filtrationthe crude product which remains is filtered chromatographically through silica gel (eluent: toluene)

Sources & evidence

ORD record
ord-addd04ba03214e9788ab586a0793e63b
Source dataset
uspto-grants-1991_10
Patent number
US05057142

Reaction notes

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