Benzenesulfonyl chloride → (Tert-butyl)[(5-chloro(1,3-thiazol-2-yl))sulfonyl]amine

HRID 38165Notes

Reaction equation

HRID 38165 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[CH:12][N:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C1(S([Cl:28])(=O)=O)C=CC=CC=1>C(OCC)C.CCOC(C)=O>[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:28])=[CH:12][N:13]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 15813414(Tert-butyl)(1,3-thiazol-2-ylsulfonyl)amineHCID 178418339Butyllithium

Product 1

HCID 22064471(Tert-butyl)[(5-chloro(1,3-thiazol-2-yl))sulfonyl]amineYield 33%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  1. stirringThe resulting suspension was stirred at room temp for 2 hr
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customchromatographed (15% EtOAc/hexane)

Sources & evidence

ORD record
ord-5aab5ff5b09f48ef923e8f62c1eb187c
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Reaction notes

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