Hydrochloric Acid → HCID 66842008, compound

HRID 253327Notes

Reaction equation

[N:1]([O-])=O.[Na+].S(=O)(=O)(O)O.[F:10][C:11]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:14][C:12]=1[NH2:13].O.O.[Sn](Cl)Cl.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[F:10][C:11]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19][CH2:20][C:21]([F:22])([F:24])[F:23])=[CH:14][C:12]=1[NH:13][NH2:1]

Participants

Conditions

Temperature: 20 °C

Procedure

53 g of sodium nitrite was added to 300 ml of concentrated sulfuric acid at 50° C. or lower, and 300 ml of acetic acid was added dropwise at 50° C. or lower. To this mixed solution, 100 ml of an acetic acid solution of 182 g of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)aniline was added dropwise over a period of 2 hours at 20° C. or lower, followed by stirring at 20° C. for 3 hours. The reaction mixture was added dropwise at 5° C. or lower to a mixed solution of 390 g of tin(II)chloride dihydrate and 1,000 ml of 6N hydrochloric acid, followed by stirring for 30 minutes. Toluene was added to this reaction mixture, and the reaction mixture was neutralized with a 10% aqueous sodium hydroxide solution. The insolubles were filtered off, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 177 g of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine.

Workup

stirringby stirring for 30 minutes
filtrationThe insolubles were filtered off
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c1bacade75ac4875818fa8624f58cc6a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872036B2

Reaction notes

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