Potassium Carbonate → 4-[(3-Methyl-1,2,4-oxadiazol-5-yl)methoxy]aniline

HRID 71342Notes

Reaction equation

[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([CH3:15])[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([CH3:15])[N:11]=2)=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 24489Sodium Dithionite

HCID 220604453-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole

Product 1

HCID 220608734-[(3-Methyl-1,2,4-oxadiazol-5-yl)methoxy]aniline

Procedure

In like manner to the preparation of 5-[(4-aminophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole, 5-(4-nitrophenoxymethyl)-3-methyl-1,2,4-oxadiazole was reacted with aqueous solution of sodium hydro sulfite and K2CO3 to prepare 5-[(4-aminophenox)ymethyl]-3-methyl-1,2,4-oxadiazole. 1H NMR (CDCl3): δ 6.82 (d, 2H, J=8.8 Hz), 6.63 (d, 2H, J=8.8 Hz), 5.15 (s, 2H), 3.38 (br s, 2H), 2.41 (s, 3H).

Sources & evidence

ORD record: ord-55e235c5dabb4ca484f85939a3c24e8d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822685B2

Reaction notes

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