Sodium Chloride → Pyridinium, 3-[2-(2-hydroxy-1-naphthalenyl)diazenyl]-1-methyl-, methyl sulfate (1:1)

HRID 1679538Notes

Reaction equation

[Cl-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]=[N:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[OH:21])[CH:4]=1.[S:22]([O:27]C)([O:25][CH3:26])(=[O:24])=[O:23]>>[CH3:26][O:25][S:22]([O-:27])(=[O:24])=[O:23].[OH:21][C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[N:10]=[N:9][C:5]1[CH:4]=[N+:3]([CH3:26])[CH:8]=[CH:7][CH:6]=1

Participants

Reactant 3

HCID 5234Sodium Chloride

HCID 6497Dimethyl Sulfate3×

HCID 737452-Naphthalenol, 1-(3-pyridinylazo)-

Product 1

HCID 135713841Pyridinium, 3-[2-(2-hydroxy-1-naphthalenyl)diazenyl]-1-methyl-, methyl sulfate (1:1)Yield 95%

Conditions

Temperature: 35 °C

Procedure

A mixture of 50.25 pounds of sodium chloride and 37 pounds (67.5 moles) or 1-(3-pyridylazo)-2-naphthol was blended in a 4.6 ft.3Littleford-Lodige precision blender and 18.75 pounds (67.5 moles) of dimethyl sulfate added thereto over a period of about 60 minutes in nine portions. The temperature of the reaction was maintained at about 35° C and the mixture blended for about 1 hour after addition of the dimethyl sulfate was complete. The crude product weighed 100 pounds (95% yield) and contained less than 0.1% of the substrate base and less than 0.01% dimethyl sulfate.

Workup

waitthe mixture blended for about 1 hour

Sources & evidence

ORD record: ord-c65395228878404fa39d9bd6f7b16370
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04081436

Reaction notes

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