Tetrahydrofuran → (Tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amine

HRID 38168

Reaction equation

HRID 38168 reaction equation
C1COCC1.[C:6]([NH:10][S:11]([C:14]1[S:15][C:16]([Cl:19])=[CH:17][CH:18]=1)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7].C([Li])CCC.C1(S(N(S(C2C=CC=CC=2)(=O)=O)[F:35])(=O)=O)C=CC=CC=1>CCCCCC>[C:6]([NH:10][S:11]([C:14]1[S:15][C:16]([Cl:19])=[CH:17][C:18]=1[F:35])(=[O:12])=[O:13])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 588007N-FluorobenzenesulfonimideHCID 101063235-Chlorothiophene-2-sulfonic acid tert-butylamideHCID 178418339Butyllithium

Product 1

HCID 22064462(Tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amineYield 108.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
23 °C

Procedure

A THF solution (1.5 mL) of 128 mg (0.50 mmol) of (tert-butyl)[(5-chloro(2-thienyl))sulfonyl]amine was cooled to −78° C. and treated with 954 μL (1.5 mmol) of a 1.6. M solution of butyl lithium in hexane. After 1 h, 159 mg (0.5 mmol) of bis(phenylsulfonyl)fluoroamine was added and the solution was allowed to warm to 23° C. The reaction was quenched with 1 mL of sat. NH4Cl, extracted 3 times with diethyl ether, dried (MgSO4), concentrated in vacuo to afford a quantitative yield (147 mg) of the desire product. 19F-NMR (CDCl3) δ (ppm): −113.4.

Workup

  1. customThe reaction was quenched with 1 mL of sat. NH4Cl
  2. extractionextracted 3 times with diethyl ether
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad29bcf1d2a34243b247630cf0dd2b6b
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Linked notes

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