2-Chloro-1,1,1-triethoxyethane → HCID 62516688, compound

HRID 732042Notes

Reaction equation

HRID 732042 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[Cl:13][CH2:14][C:15](OCC)(OCC)OCC>>[Cl:13][CH2:14][C:15]1[O:5][C:4]([C:3]2[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:2]=2[F:1])=[N:6][N:7]=1

Participants

3

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 54690782HCID 54690782, compound

Product 1

HCID 62516688HCID 62516688, compoundYield 66%

Procedure

2-Fluoro-5-methyl-benzoic acid hydrazide (320 mg, 1.9 mmol) and 2-chloro-1,1,1-triethoxy-ethane (1.9 ml) were heated in a sealed vial at 120° C. for 30 min. The reaction mixture was place directly onto a flash column (silica gel) and purified by using 0-5% ethyl acetate in hexanes to afford 2-chloromethyl-5-(2-fluoro-5-methyl-phenyl)-[1,3,4]oxadiazole (284.5 mg, 66%). 1H NMR (CDCl3) d (ppm): 7.89 (q, 1H), 7.36 (m, 1H), 7.16 (t, 1H), 4.81 (s, 2H), 2.43 (s, 3H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-a0b8fbedb23443eca0eebd602b59dfa5
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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