Hydrochloric Acid → HCID 68886240, compound

HRID 1294352Notes

Reaction equation

HRID 1294352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][C:9](N(C)C)=O.C[O-].[Na+].ClC[C:24]1[CH:25]=[C:26]([CH:41]=[CH:42][CH:43]=1)[O:27][CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][C:42]1[CH:43]=[CH:24][CH:25]=[C:26]([O:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])[CH:41]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 10942334Sodium MethoxideHCID 15840683HCID 15840683, compound

Product 1

HCID 68886240HCID 68886240, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of methyl [3-chloro-4-[(dimethylamino)carbonylthio]phenyl]acetate (0.80 g), a 28% solution of sodium methoxide in methanol (0.75 g) and methanol (20 mL) was stirred with heating under reflux for 2 hrs. 4-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.87 g) was added to the reaction mixture at room temperature and the mixture was further stirred for 12 hrs. The reaction mixture was poured into 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-[3-chloro-4-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetate as a colorless oil (0.48 g, yield 35%), from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1b84e7f910d4f018c0036905cfd87c4
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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