4-Nitrobenzenesulfonyl chloride → HCID 771980, compound

HRID 1907735Notes

Reaction equation

HRID 1907735 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C1COCC1.C(Cl)Cl>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 100093-AminopyridineHCID 218852-Dimethylaminopyridine

Product 1

HCID 771980HCID 771980, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminopyridine 244 (3.03 g, 32.23 mmol) in THF (70 mL) and DCM (135 mL) was added 4-nitrobenzene sulfonyl chloride 245 (1.5 g, 67.68 mmol), triethylamine (7.17 g, 70.9 mmol) and dimethylamino pyridine (catalytic amount). The reaction mixture was allowed to stir at room temperature for 1 h then concentrated. The residue was taken up in MeOH (200 mL) then solid sodium methoxide (20 g) was added and the reaction mixture was stirred at 50° C. for 3 h, carefully neutralized with 1N HCl until pH 7. The formed precipitate was collected by filtration to give the title compound 246 (7.67 g, 85% yield).

Workup

  1. concentrationthen concentrated
  2. additionsolid sodium methoxide (20 g) was added
  3. stirringthe reaction mixture was stirred at 50° C. for 3 h
  4. filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-d1b6c318bfd945a8adbd50c6aa38558f
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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