Tert-Butylamine → 5-Chlorothiophene-2-sulfonic acid tert-butylamide

HRID 900298

Reaction equation

HRID 900298 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>C1COCC1.C(OCC)C>[C:11]([NH:15][S:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:8])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 27339255-Chlorothiophene-2-sulfonyl chloride

Product 1

HCID 101063235-Chlorothiophene-2-sulfonic acid tert-butylamideYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5.5 g (27.5 mmol) of 5-chlorothiophenesulfonyl chloride in dry THF at 0° C. was treated with a solution of 5.7 mL (75.5 mmol) of t-butylamine. After warming to 23° C., the reaction mixture was diluted with 125 mL of diethyl ether, filtered, and washed with 1 N HCl, brine, and dried (MgSO4). Concentration in vacuo affords 6.4 g (98%) of the named compound as an oil.

Workup

  1. filtrationfiltered
  2. washwashed with 1 N HCl, brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-7fd5b4757d274a38ad4b901d4a492cad
Source dataset
uspto-grants-2008_04
Patent number
US07358257B2

Linked notes

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