反応 #66443

反応方程式

benzenesulfonyl chloride

(tert-butyl)(1,3-thiazol-2-ylsulfonyl)amine

n-butyllithium

→

desired compound

収率 33.0%

(tert-butyl)[(5-chloro(1,3-thiazol-2-yl))sulfonyl]amine

収率 33.0%

溶媒

EtOAc

—

hexanes

ethyl ether

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting suspension was stirred at room temp for 2 hr
2. 2
   洗浄washed with water and brine
3. 3
   その他dried
4. 4
   濃縮concentrated in vacuo
5. 5
   その他chromatographed (15% EtOAc/hexane)

実験手順

To a solution of (tert-butyl)(1,3-thiazol-2-ylsulfonyl)amine (0.15 g, 0.7 mmol) in ethyl ether (3 mL) at −78° C. was added a 1.6M solution of n-butyllithium (0.875 mL, 1.4 mmol) in hexanes via syringe under argon: The reaction mixture was stirred at −78° C. for 1 hr, then neat benzenesulfonyl chloride (90 μL, 0.7 mmol) was added. The resulting suspension was stirred at room temp for 2 hr. The reaction was diluted with EtOAc, washed with water and brine, dried, concentrated in vacuo and chromatographed (15% EtOAc/hexane) to give pure desired compound (58 mg, 33%). ES-MS (M+Na)+=277, 279 (Cl), (M−tBu+H)+=199, 201 (Cl).

出典