Triethylamine → 2-tert-Butyl-6-chloro-7-(4-methylpiperazine-1-sulfonyl)-benzooxazole

HRID 1840333Notes

Reaction equation

HRID 1840333 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([S:14](Cl)(=[O:16])=[O:15])=[C:12]([Cl:18])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C1COCC1>[C:1]([C:5]1[O:6][C:7]2[C:13]([S:14]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)(=[O:16])=[O:15])=[C:12]([Cl:18])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

Product 1

HCID 234478362-tert-Butyl-6-chloro-7-(4-methylpiperazine-1-sulfonyl)-benzooxazoleYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (2.69 g, 8.73 mmol) and triethylamine (2.44 mL, 17.5 mmol) in THF (60 mL) at 0° C. was added 1-methylpiperazine (0.98 mL, 8.83 mmol). The reaction was warmed to room temperature and allowed to stir overnight. The solution was concentrated and then diluted with water and extacted with ethyl acetate (3 times). The combined organic layers were dried with MgSO4, filtered, and concentrated. Flash chromatography (80% ethyl acetate/20% Ethanol) on silica gel gave the title compound (2.45 g, 76%). EI-MS m/z 372(M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bba74d741e7043a78bbdd1d7da003d99
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

Loading…