Hydrochloric Acid → HCID 66908075, compound

HRID 1691515Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[N+:22]([O-])=O)[C:4]=1[OH:25].[OH-].[Na+].C(S(O)=O)(N)=N.Cl>O.C(O)C>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]3=[N:22]2)[C:4]=1[OH:25]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 1 L round bottom flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet was added 26.0 g (73.2 mmol) 2-(hydroxymethyl)-4-methyl-6-((2-nitro-4-(trifluoromethyl)phenyl)-diazenyl)phenol and 300 ml ethanol. Sodium hydroxide (17.6 g, 441 mmol) was dissolved in 100 ml deionized water and approximately one fourth was added dropwise to the azo mixture. The reaction mixture was heated to 80° C. and 23.9 g (221 mmol) formamidinesulfinic acid and the remaining sodium hydroxide solution were added to the azo mixture over 30 minutes. The reaction mixture was heated at 80° C. for 3 hours, poured in 3 L deionized water, and acidified to pH 4 using 1N HCl. The solid was collected by vacuum filtration, washed with ample amounts of water, and then dried for 20 hours under vacuum (0.1 mm Hg) at 42° C. to give 18.6 g (79%) of an off white solid.

Workup

customIn a 1 L round bottom flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet
temperatureThe reaction mixture was heated at 80° C. for 3 hours
additionpoured in 3 L
filtrationThe solid was collected by vacuum filtration
washwashed with ample amounts of water
customdried for 20 hours under vacuum (0.1 mm Hg) at 42° C.
customto give 18.6 g (79%) of an off white solid

Sources & evidence

ORD record: ord-e87fc9ea451d4c7fb653b087fe382651
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153703B2

Reaction notes

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