Hydrochloric Acid → HCID 86591691, compound

HRID 1295337Notes

Reaction equation

HRID 1295337 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:7])[N:6]=1.Cl[CH2:14][C:15]1[CH:16]=[C:17]([CH:32]=[C:33]([O:35][CH2:36][CH3:37])[CH:34]=1)[O:18][CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[CH2:36]([O:35][C:33]1[CH:34]=[C:15]([CH:16]=[C:17]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])[CH:32]=1)[CH2:14][S:1][C:2]1[S:3][C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:7])[N:6]=1)[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 229306794-(3-Chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 178499653HCID 178499653, compound

Product 1

HCID 86591691HCID 86591691, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl (2-mercapto-4-methylthiazol-5-yl)acetate (455 mg), 4-(3-chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole (800 mg), potassium carbonate (465 mg) and N,N-dimethylformamide (20 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl [2-[3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylthio]-4-methylthiazol-5-yl]acetate (1.02 g, yield 87%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8f676d0f38846f5bfa017ce3e673e05
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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