Hydrochloric Acid → HCID 29795223, compound

HRID 536053Notes

Reaction equation

HRID 536053 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].Cl.CN.[CH2:19]([N:21](CC)CC)C.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[S:12]([NH:21][CH3:19])(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 49621612,4-Difluoro-5-nitrobenzenesulfonyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 29795223HCID 29795223, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 2,4-difluoro-5-nitrobenzenesulfonyl chloride (21 g, 81 mmol) in THF (400 mL) at −60° C. was treated with methylamine hydrochloride (6.6 g, 97 mmol) and then treated dropwise with triethylamine (22.6 mL, 162 mmol). After stirring for 6 hours at −60 to −40° C. the mixture was adjusted to pH 3 with the addition of 15% aqueous HCl, diluted with water, and extracted with EtOAc. The organic extracts were dried (Na2SO4), concentrated, and subjected to flash chromatography (17% EtOAc-petroleum ether) to give 2,4-difluoro-N-methyl-5-nitrobenzenesulfonamide (8 g, 38%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.66-8.74 (m, 1 H), 7.20-7.25 (m, 1 H), 4.81-4.91 (m, 1 H), 2.78-2.81 (m, 3 H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e02c72a148cb49d2bf5c85e2db809760
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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