Phenol, 4-methoxy-2-nitro- → 3-Methyl-5-[7-(2-nitro-4-methoxyphenoxy)heptyl]isoxazole

HRID 544619Notes

Reaction equation

HRID 544619 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:13][N:12]=[C:11]([CH3:14])[CH:10]=1.[Na].[N+:16]([C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[OH:27])([O-:18])=[O:17]>>[CH3:14][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:27][C:20]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])[O:13][N:12]=1

Participants

4

Reactant 3

HCID 15285Phenol, 4-methoxy-2-nitro-HCID 5360545SodiumHCID 133169675-(7-Bromoheptyl)-3-methylisoxazole

Product 1

HCID 52712053-Methyl-5-[7-(2-nitro-4-methoxyphenoxy)heptyl]isoxazole

Procedure

[I; R is CH3, n is 7, X is O, Ar is 2--O2N--4--CH3OC6H3 ] was prepared from 4.0 g of 5-(7-bromoheptyl)-3-methylisoxazole (Example 37a) and 2.94 g of the sodium salt of 2-nitro-4-methoxyphenol according to the procedure of Example 37, part (b), and was obtained in the form of a yellow solid (4.0 g), m.p. 51° C. when recrystallized from an ether-hexane mixture; MIC vs. rhinovirus Type 2 in vitro=0.3 μg/ml; and vs. polio-2 virus=0.17 μg/ml.

Sources & evidence

ORD record
ord-5f13ab7db3bc45e08014ba94ec5b3406
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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