Hydrochloric Acid → HCID 81562135, compound

HRID 1052515Notes

Reaction equation

HRID 1052515 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](=O)(O)[O-].[Na+].[S:17](Cl)(Cl)(=[O:19])=[O:18].Cl>>[Br:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([NH:1][S:17]([CH3:12])(=[O:19])=[O:18])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 115696043-Amino-5-bromobenzoic acid

Product 1

HCID 81562135HCID 81562135, compound

Procedure

3-Amino-5-bromobenzoic acid (1 g, 4.63 mmol, prepared according to EP 2394998 A1 20111214) was suspended in a saturated solution of sodium bicarbonate (6.4 ml). Sulfonyl chloride (0.54 ml, 6.94 mmol) was added dropwise at 0° C. After 2 h of stirring at this temperature, concentrated HCl was added dropwise to the reaction mixture until pH=7 and the resultant dissolution was directly purified by reverse phase chromatography using SP1® Purification System (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%), to obtain 360 mg of the final compound as a white solid. Purity: 99%

Workup

  1. additionwas added dropwise to the reaction mixture until pH=7
  2. dissolutionthe resultant dissolution
  3. customwas directly purified by reverse phase chromatography
  4. customSP1® Purification System (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid

Sources & evidence

ORD record
ord-94519cc9f5634c15856ffaab4511a325
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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