Pyridine → HCID 68434859, compound

HRID 2224083Notes

Reaction equation

HRID 2224083 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[OH:17].N1C=CC=CC=1.[Br:24][C:25]([CH3:30])([CH3:29])[C:26](Cl)=O>C(OCC)(=O)C>[C:11]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH2:26][C:25]([Br:24])([CH3:30])[CH3:29])=[C:3]([OH:17])[CH:4]=2)(=[O:10])=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 111060492-Bromo-2-methylpropanoyl chlorideHCID 14053206HCID 14053206, compound

Product 1

HCID 68434859HCID 68434859, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-5-benzenesulfonyl-phenol (1.06 g., 4.26 mmol) in 8 mL ethyl acetate was added pyridine (0.345 mL, 4.26 mmol). The solution was cooled to 0° C. and 2-bromo-2-methyl-propionyl chloride (0.553 mL, 4.47 mmol) was added dropwise and stirring was continuted for 2 hours. The reaction mixture was diluted with 50 mL ethyl acetate and washed with 50 mL 10% aqueous hydrogen chloride, 50 mL saturated aqueous sodium bicarbonate, 50 mL water, then 50 mL brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to yield 5-benzenesulfonyl-2-(2-bromo-2-methyl-propylamino)-phenol as a crude oil, which was used directly in the following step.

Workup

  1. washwashed with 50 mL 10% aqueous hydrogen chloride, 50 mL saturated aqueous sodium bicarbonate, 50 mL water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1955418cbc974cb6a37a586ff6461458
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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