Water → 6-Amino-3-chloro-2-(4-methyl-piperazine-1-sulfonyl)-phenol

HRID 1840334Notes

Reaction equation

HRID 1840334 reaction equation
C(C1[O:6][C:7]2[C:13]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[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[CH2:22][CH2:21][N:20]([CH3:23])[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 234478362-tert-Butyl-6-chloro-7-(4-methylpiperazine-1-sulfonyl)-benzooxazole

Product 1

HCID 234478576-Amino-3-chloro-2-(4-methyl-piperazine-1-sulfonyl)-phenolYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-tert-Butyl-6-chloro-7-(4-methyl-piperazine-1-sulfonyl)-benzooxazole (2.44 g, 6.56 mmol) in 1,4-dioxane (20 mL) was treated with water (4 mL) and conc. H2SO4 (4 mL). The mixture was heated to 85° C. for 14 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 (1.35 g, 68%). EI-MS m/z 306(M+H)+.

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-515b1f6ad5e64c049f8435b8276ecfb3
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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