Hydrochloric Acid → HCID 66878089, compound

HRID 923019Notes

Reaction equation

HRID 923019 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66877783HCID 66877783, compound

Product 1

HCID 66878089HCID 66878089, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.01 g of tert-butyl 4-(bromomethyl)-2-chlorobenzoate was reacted via Procedure O to give tert-butyl 2-chloro-4-(methylsulfonylmethyl)benzoate. 1.2 g of tert-butyl 2-chloro-4-(methylsulfonylmethyl)benzoate was treated with 10 mL of 4N HCl in Dioxane at 45° C. and concentrated upon completion to give crude 2-chloro-4-(methylsulfonylmethyl)benzoic acid. 775 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 1 g of 2-chloro-4-(methylsulfonylmethyl)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to give pure 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)benzamide. MS (Q1) 435 (M)+.

Workup

  1. concentrationconcentrated upon completion

Sources & evidence

ORD record
ord-e93fa9d7af654e8ea029ad120adb7088
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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