Sulfuric Acid → Thiocyanic acid, 4-methoxy-2-nitrophenyl ester

HRID 1750090Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][C:9]=1N)([O-:3])=[O:2].OS(O)(=O)=O.N([O-])=O.[Na+].[S-:22][C:23]#[N:24].[K+]>O.[Co](Cl)Cl>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][C:9]([S:22][C:23]#[N:24])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A sample of 3-nitro-4-aminoanisole (13.5 g, 80 mmol) was dissolved in water (100 mL) and concentrated H2SO4 (44 mL), cooled to 0° C., and diazotized with a solution of sodium nitrite (14.3 g, 207.2 mmol) in water (25 mL) while maintaining a temperature no greater than 5° C. The resulting solution was added dropwise with vigorous stirring to a solution of crystalline cobalt chloride (42 g, 176 mmol) and potassium thiocyanate (25.6 g, 264 mmol) in water (100 mL), after which the mixture was stirred at 0-10° C. for 3 h and allowed to stand overnight. It was then stirred at 50° C. for 16 h until nitrogen evolution had ceased. The precipitate was removed by filtration, washed with water, and dried at 80° C. to give 4-methoxy-2-nitro-1-thiocyanatobenzene (intermediate 22) (9.82 g, 58%). mp: 127-128° C.

Workup

temperaturewhile maintaining a temperature no greater than 5° C
additionThe resulting solution was added dropwise
waitto stand overnight
stirringIt was then stirred at 50° C. for 16 h until nitrogen evolution
customThe precipitate was removed by filtration
washwashed with water
customdried at 80° C.

Sources & evidence

ORD record: ord-93bf5f306360456d8a328700ee0ecb85
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156822B2

Reaction notes

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