Isopropylamine → 2-cyano-3-fluoro-N-isopropylbenzenesulphonamide

HRID 1701841Notes

Reaction equation

HRID 1701841 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5]([C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[S:14](Cl)(=[O:16])=[O:15])#[N:6]>C(OCC)C>[C:5]([C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[S:14]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:16])=[O:15])#[N:6]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 205052122-Cyano-3-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 205052112-cyano-3-fluoro-N-isopropylbenzenesulphonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5.2 ml of isopropylamine in 50 ml of diethyl ether cooled in an ice bath, a solution of 4.4 g of 2-cyano-3-fluorobenzenesulphonylchloride in 50 ml of diethylether was added dropwise while stirring; reaction temperature approx. 5° C. After leaving to stand at room temperature for one hour, the reaction mixture was washed twice with ice water, dried on anhydrous Na2SO4, filtered and evaporated to dryness. The desired product was obtained in a yield of 4.16 g; melting-point 97°-105° C.

Workup

  1. customreaction temperature approx. 5° C
  2. customAfter leaving
  3. washthe reaction mixture was washed twice with ice water
  4. dry with materialdried on anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-41d78f76556b4f499753c37442878997
Source dataset
uspto-grants-1983_04
Patent number
US04379157

Reaction notes

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