Hydrochloric Acid → 4-chloro-5-(2,4-dichlorophenoxy)benzo-2,1,3-oxadiazole N-oxide

HRID 463617Notes

Reaction equation

CC([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:6]=1[Cl:23])=O.Cl.ClC1C(OC2C=CC(Cl)=CC=2Cl)=CC=C([N+]([O-])=O)C=1N.[OH-].[K+].Cl[O-].[Na+]>>[Cl:23][C:6]1[C:5]2[C:10](=[N+:11]([O-:13])[O:12][N:4]=2)[CH:9]=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 202643442-Chloro-3-(2,4-dichlorophenoxy)-6-nitroaniline

HCID 20264352N-methylcarbonyl 2-chloro-3-(2,4-dichlorophenoxy)-6-nitroaniline

HCID 23665760Sodium Hypochlorite

Product 1

HCID 537502744-chloro-5-(2,4-dichlorophenoxy)benzo-2,1,3-oxadiazole N-oxide

Procedure

Following the procedure of Example 4, N-methylcarbonyl 2-chloro-3-(2,4-dichlorophenoxy)-6-nitroaniline is converted, by reaction with HCl, to 2-chloro-3-(2,4-dichlorophenoxy)-6-nitroaniline, which is then reacted with potassium hydroxide and sodium hypochlorite, again following Example 4 procedures, to yield the final product, 4-chloro-5-(2,4-dichlorophenoxy)benzo-2,1,3-oxadiazole N-oxide.

Sources & evidence

ORD record: ord-04bce43b8f9d420aa740cc9c2e7931dd
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04544400

Reaction notes

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