Epichlorohydrin → HCID 57508926, compound

HRID 1665968Notes

Reaction equation

HRID 1665968 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:24][CH2:23][C:5]2=[C:6]([C:9]3[O:13][N:12]=[C:11]([C:14]4[CH:19]=[C:18]([CH3:20])[C:17]([OH:21])=[C:16]([CH3:22])[CH:15]=4)[N:10]=3)[S:7][CH:8]=[C:4]2[CH2:3]1.[OH-].[Na+].[CH2:28]([CH:30]1[O:32][CH2:31]1)Cl>C(O)(C)C.O>[CH3:22][C:16]1[CH:15]=[C:14]([C:11]2[N:10]=[C:9]([C:6]3[S:7][CH:8]=[C:4]4[CH2:3][C:2]([CH3:25])([CH3:1])[CH2:24][CH2:23][C:5]=34)[O:13][N:12]=2)[CH:19]=[C:18]([CH3:20])[C:17]=1[O:21][CH2:28][CH:30]1[CH2:31][O:32]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 135968114HCID 135968114, compound

Product 1

HCID 57508926HCID 57508926, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-[5-(5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (35 mg, 1.18 mmol) in isopropanol (17 mL) is treated with 2 N aq. NaOH (8.6 mL) followed by epichlorohydrine (660 mg, 7.14 mmol). The mixture is stirred at 50° C. for 18 h before it is diluted with water and extracted twice with EA. The combined organic extracts are dried over Na2SO4, filtered, evaporated and dried to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazole (480 mg) as a pale yellow oil; LC-MS: tR=1.24 min, [M+1]+=411.31.

Workup

  1. extractionextracted twice with EA
  2. dry with materialThe combined organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried

Sources & evidence

ORD record
ord-b551eb8bdc4d441a9cf81a083744d8c3
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

Loading…