Citric Acid → 5-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide

HRID 1927982Notes

Reaction equation

HRID 1927982 reaction equation
CC[N:3](CC)CC.[Br:8][C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[N:13][CH:14]=1.C(O)(=O)[CH2:20][C:21]([CH2:26]C(O)=O)([C:23](O)=[O:24])O>C1COCC1>[OH:24][CH2:23][C:21]([NH:3][S:15]([C:11]1[CH:12]=[N:13][CH:14]=[C:9]([Br:8])[CH:10]=1)(=[O:17])=[O:16])([CH3:26])[CH3:20]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 8471TriethylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 602093435-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of commercially available 2-amino-2-methyl-1-propanole (478 mg, 5 mmol) and Et3N (0.75 mL, 5 mmol) in THF (50 mL) at 0° C. was added portionwise added 5-bromo-pyridine-3-sulfonyl chloride [CAS-No. 65001-21-0] (according to J. Org. Chem. 1989, 54(2), 389) (1.28 g, 5 mmol) and the mixture was stirred at 23° C. for 1 h. The reaction is worked up by neutralization with 5% citric acid, extracted with EtOAc, washed with sat. NaHCO3-sol. and brine, dried over Na2SO4, filtered and concentrated to give a light brown solid, which was purified by trituration with heptane/diethyl ether gave the title compound as a white solid (1.25 g, 82%). MS (ISP) 309.2 [(M+H)+], 311.1 [(M+2+H)+]; mp 112° C.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with sat. NaHCO3-sol
  3. dry with materialand brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light brown solid, which
  7. customwas purified by trituration with heptane/diethyl ether

Sources & evidence

ORD record
ord-c9f0c30005684f08846fe3ce1f81c9c6
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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