4-Aminosalicylic Acid → HCID 135510740, compound

HRID 1640396Notes

Reaction equation

N[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[N:12]([O-])=O.[Na+].[C:16]1([C:22]2[S:26][S:25][C:24](=[S:27])[CH:23]=2)[CH:21]=[CH:20]C=[CH:18][CH:17]=1.C[N:29]([CH3:32])C=O>Cl.O>[OH:11][C:4]1[CH:3]=[CH:2][C:10]([N:12]=[N:29][C:32]2[CH:20]=[CH:21][C:16]([C:22]3[S:26][S:25][C:24](=[S:27])[CH:23]=3)=[CH:17][CH:18]=2)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Amino-2-hydroxy-benzoic acid (1, 1 mmol) was dissolved in a mixture of 10 mL of concentrated HCl and 5 mL of water and diazotized with a solution of sodium nitrite (1 mmol). The diazo suspension is added in portions to a solution of 5-phenyl-[1,2]dithiole-3-thione (1 mmol) in dimethylformamide. After 2 days the reaction mixture is heated for 30 min at 50° C. After cooling the azo compound (2) was precipitated by means of HCl and filtered off (yield 65%), to yield the compound of Formula II, 2-Hydroxy-5-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenylazo]-benzoic acid.

Workup

customwas precipitated by means of HCl
filtrationfiltered off (yield 65%)

Sources & evidence

ORD record: ord-87e85eb27fe3401c9a9cd7c947d924f6
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114857B2

Reaction notes

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