Dimethyl Sulfate → HCID 21536758, compound

HRID 1076453Notes

Reaction equation

HRID 1076453 reaction equation
F[As-](F)(F)(F)(F)F.[CH3:8][N:9]([CH3:25])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]#[N:17])=[CH:12][C:11]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O(C1C=CC=CC=1N)C1C=CC=CC=1.S(OC)(OC)(=O)=O.CN(C)C1C=CC=CC=1OC1C=CC=CC=1.[Cl-].[Cl:64][C:65]1[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][C:66]=1[N+]#N>>[Cl:64][C:65]1[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][C:66]=1[N:17]=[N:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]([CH3:25])[CH3:8])=[C:11]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]=1

Participants

6

Reactant 5

HCID 6497Dimethyl SulfateHCID 75899Benzenamine, 2-phenoxy-HCID 11805943Benzenediazonium, 2,5-dichloro-, chlorideHCID 21536777HCID 21536777, compoundHCID 21536798HCID 21536798, compound

Product 1

HCID 21536758HCID 21536758, compound

Procedure

4-Dimethylamino-3-phenoxybenzenediazonium hexafluoroarsenate was also prepared by the following route: o-phenoxyaniline was methylated with dimethyl sulfate to N,N-dimethyl-o-phenoxyaniline, m. 34°-5°, which was coupled with 2,5-dichlorobenzenediazonium chloride to give 4-(2,5-dichlorophenylazo)-N,N-dimethyl-2-phenoxyaniline, m. 93°-4°. This was then reduced catalytically to N1,N1 -dimethyl-2-phenoxy-p-phenylenediamine, m. 76°-6°, which was diazotized as above.

Workup

  1. custom34°-5°, which

Sources & evidence

ORD record
ord-a188478fd7b24194845f65914bb05fbe
Source dataset
uspto-grants-1976_05
Patent number
US03957489

Reaction notes

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