Water → HCID 23447752, compound

HRID 1840391Notes

Reaction equation

HRID 1840391 reaction equation
C(C1[O:6][C:7]2[C:13]([S:14]([N:17]3[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)(=[O:16])=[O:15])=[C:12]([Cl:24])[CH:11]=[CH:10][C:8]=2[N:9]=1)(C)(C)C.O.OS(O)(=O)=O.[OH-].[Na+]>O1CCOCC1>[NH2:9][C:8]1[C:7]([OH:6])=[C:13]([S:14]([N:17]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])[C:12]([Cl:24])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23447843HCID 23447843, compound

Product 1

HCID 23447752HCID 23447752, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-tert-Butyl-6-chloro-7-(homopiperazine-1-sulfonyl)-benzooxazole (2.0 g, 4.24 mmol) in 1,4-dioxane (56 mL) was treated with water (3.5 mL) and conc. H2SO4 (3.5 mL). The mixture was heated to 100° C. for 16 h. The reaction was cooled to room temperature, and then basified to pH=14 with 25% aq NaOH. washed. The mixture was extracted with ethyl acetate (3 times), dried with MgSO4, filtered, and concentrated to afford the title compound (1.04 g, 80%). EI-MS m/z 306.2(M+).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed
  3. extractionThe mixture was extracted with ethyl acetate (3 times)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0ddf5b564c0425e9e208a0b005fecfd
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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