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

HRID 1393059Notes

Reaction equation

HRID 1393059 reaction equation
[CH3:1][SH:2].[Na].F[C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11].C(O)C.Cl>O>[CH3:1][S:2][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27374205-Fluoro-2-nitrobenzoic acidHCID 45051789Methylmercaptan sodium

Product 1

HCID 89345765-(Methylsulfanyl)-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.5 mL of 15% sodium methylmercaptan aqueous solution was added to the mixture of 11.0 g (5.40 mmol) of 5-fluoro-2-nitrobenzoic acid and 5 mL of ethanol and stirred for 2 days. Then, 10 mL of water was added and pH thereof was adjusted to become 1 by concentrated hydrochloric acid. After filtering out the precipitated compound, it was washed with water, ether and hexane and dried to obtain a crude material of 5-methylthio-2-nitrobenzoic acid. 3 mL of thionyl chloride was added to the obtained crude material and stirred for 5 hours. The thionyl chloride was removed to obtain the title compound.

Workup

  1. filtrationAfter filtering out the precipitated compound, it
  2. washwas washed with water, ether and hexane
  3. customdried

Sources & evidence

ORD record
ord-02ac60454c004a4b9ef7592bb55373fb
Source dataset
uspto-grants-2008_03
Patent number
US07345049B2

Reaction notes

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