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

HRID 1050987Notes

Reaction equation

HRID 1050987 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:15]([C:19]1[O:20][C:21]2[C:27]([S:28](Cl)(=[O:30])=[O:29])=[C:26]([Cl:32])[CH:25]=[CH:24][C:22]=2[N:23]=1)([CH3:18])([CH3:17])[CH3:16].O>O1CCCC1>[C:15]([C:19]1[O:20][C:21]2[C:27]([S:28]([N:12]3[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]3)(=[O:30])=[O:29])=[C:26]([Cl:32])[CH:25]=[CH:24][C:22]=2[N:23]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 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 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.62 ml (11.68 mmol; 1.2 eq) of triethylamine followed by 1.20 ml (10.71 mmol; 1.1 eq) of 1-methylpiperazine were added to a solution of 3.0 g (9.73 mmol; 1.0 eq) of 2-tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride (commercial ?) in 45 ml of tetrahydrofuran. The reaction medium was stirred at ambient temperature for 2 hours. Water was added and the reaction medium was extracted with ethyl acetate. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated. 3.57 g of 2-tert-butyl-6-chloro-7-(4-methylpiperazine-1-sulfonyl)benzooxazole were obtained in the form of a tacky brown foam. Yield=98%.

Workup

  1. extractionthe reaction medium was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9362f4fff4804733a378377229d494bf
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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