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

HRID 1989259Notes

Reaction equation

HRID 1989259 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].CCN(CC)CC.[Br:14][C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[N:19][CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[OH:4][CH2:3][C:2]([NH:1][S:21]([C:17]1[CH:18]=[N:19][CH:20]=[C:15]([Br:14])[CH:16]=1)(=[O:23])=[O:22])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 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-propanol (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-1324a9e89f3b4a94b33f3f20b01ed01a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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