Benzenesulfonyl chloride → HCID 15453200, compound

HRID 842879Notes

Reaction equation

HRID 842879 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])[O:4][N:3]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.ClCCl>[Br:7][C:6]1[C:2]([NH:1][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])=[N:3][O:4][C:5]=1[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 15453199HCID 15453199, compound

Product 1

HCID 15453200HCID 15453200, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-Amino-4-bromo-5-tert-butylisoxazole (219 mg, 1.0 mmol) was dissolved in dry pyridine (1 ml). Benzenesulfonyl chloride (0.14 ml, 1.1 mmol) and 4-dimethylamino-pyridine (5 mg) were added and the solution was stirred at 50° C. for 6 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1 N HCl (50 ml) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography (9:1 hexanes/ethyl acetate). A crystalline solid was obtained after recrystallization from ethyl acetate/hexanes, m.p. 139-141° C.

Workup

  1. washwashed with 1 N HCl (50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ecccd105792c4b5898cb58931d778a36
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

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