Hydrochloric Acid → 5-(Methylsulfanyl)-2-nitrobenzoic acid

HRID 2268772Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7](O)=O.[OH-:14].[Na+].[OH2:16].[OH2:17].[OH2:18].O.O.O.O.O.O.[S-2:25].[Na+].[Na+].S(OC)(O[CH3:32])(=O)=O.Cl>O>[CH3:32][S:25][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:18])=[O:17])=[C:6]([CH:10]=1)[C:7]([OH:16])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

5-Chloro-2-nitrobenzoic acid (25.2 g, 0.125 mol) was stirred in water. To this was added sufficient sodium hydroxide solution (2M, 42 ml, 0.084 mol) to dissolve the acid completely. A solution of sodium sulfide nonahydrate (33.0 g, 0.1375 mol) in water (75 ml) was added and the solution was stirred at 60° C. for 2.5 hr. This resultant red solution was added to a solution of sodium hydroxide (50% 10 ml, 0.125 mol) in water (15 ml), dimethyl sulfate (24 ml, 0.25 mol) was added and the solution heated under reflux for 1 hour. The solution was cooled and acidified with hydrochloric acid (5M, 32 ml, 0.16 mol). The precipitated yellow solid was filtered off, washed with water, dried at 60° C. under vacuum, mp 173° C. (lit. J. Heterocyclic Chemistry 1981 18 117). Mp 175-178° C.)

Workup

dissolutionto dissolve the acid completely
additionwas added
temperaturethe solution heated
temperatureunder reflux for 1 hour
temperatureThe solution was cooled
filtrationThe precipitated yellow solid was filtered off
washwashed with water
dry with materialdried at 60° C. under vacuum, mp 173° C. (lit. J. Heterocyclic Chemistry 1981 18 117)

Sources & evidence

ORD record: ord-70efc4f861044d6da29849b2c8d77509
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329366B1

Reaction notes

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