Triethylamine → 2-tert-Butyl-6-chloro-N-methoxy-N-methyl-1,3-benzoxazole-7-sulfonamide
Reaction equation
[CH3:1][NH:2][O:3][CH3:4].C(N(CC)CC)C.[C:12]([C:16]1[O:17][C:18]2[C:24]([S:25](Cl)(=[O:27])=[O:26])=[C:23]([Cl:29])[CH:22]=[CH:21][C:19]=2[N:20]=1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[CH3:4][O:3][N:2]([CH3:1])[S:25]([C:24]1[C:18]2[O:17][C:16]([C:12]([CH3:14])([CH3:13])[CH3:15])=[N:20][C:19]=2[CH:21]=[CH:22][C:23]=1[Cl:29])(=[O:26])=[O:27]Participants
Conditions
- Temperature
- 0 °C
Procedure
N,O-dimethylhydroxylamine (1.98 g, 2 equiv) was suspended in dry THF (20 ml) and cooled to 0° C. in an ice bath while stirring vigourously. Triethylamine (4.51 ml, 2 equiv) was added maintaining the temperature at 0° C. followed by dropwise addition of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (US 2007/0249672 page 9) (5 g, 16.22 mmol, 1 equiv) in THF (10 ml) over 30 minutes. The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to room temperature overnight. The resulting mixture was filtered and concentrated in vacuo and the resulting solid was dissolved in EtOAc (75 ml), washed with water (3×20 ml), sat. brine (30 ml) dried (MgSO4) and concentrated in vacuo to afford the title compound as a solid; [M+H]+ 333.
Workup
- temperaturemaintaining the temperature at 0° C.
- stirringThe reaction mixture was stirred at 0° C. for 1 h
- temperatureto warm to room temperature overnight
- filtrationThe resulting mixture was filtered
- concentrationconcentrated in vacuo
- dissolutionthe resulting solid was dissolved in EtOAc (75 ml)
- washwashed with water (3×20 ml), sat. brine (30 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-87f19b3afe2d40c0b5e932f98626bdea
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115087B2
Reaction notes
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