Hydrochloric Acid → HCID 838180, compound

HRID 1776579Notes

Reaction equation

HRID 1776579 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].Cl>C(Cl)Cl.O>[OH:12][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 1

HCID 838180HCID 838180, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-amino-2-hydroxybenzoate (9.58 g, 57.3 mmol) in DCM (150 ml), pyridine (9.27 ml, 115 mmol) was added followed by methanesulfonyl chloride (4.47 ml, 57.3 mmol). The reaction mixture was stirred at RT for 4 hours. Water (50 ml) and HCl 6M (15 ml) were added, and the resulting precipitate was collected by filtration, washed with water and dried to give methyl 2-hydroxy-5-(methylsulfonamido)benzoate (13 g, 53.0 mmol, 92% yield, MS/ESI+ 246.0 [MH]+).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-6e0aa20eb37e4c4381a69ab4902913b2
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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