4-Nitrobenzenesulfonyl chloride → HCID 3112496, compound

HRID 1841953Notes

Reaction equation

HRID 1841953 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH2:19][CH2:18][CH:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:11]1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C1COCC1>[CH3:17][O:16][C:14]([CH:13]1[CH2:18][CH2:19][N:10]([S:29]([C:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=2)(=[O:30])=[O:31])[CH2:11][CH2:12]1)=[O:15]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotate

Product 1

HCID 3112496HCID 3112496, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (9.4 ml, 54.1 mmol) was added in one portion to a stirred solution of methyl isonipecotate (6.78 g, 47.4 mmol) in THF (100 ml) at room temperature. To this mixture was added 4-nitrobenzenesulfonyl chloride (10.0 g, 45.1 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time, the resulting solid precipitate was collected by filtration and washed with cold THF (50 ml) before being dried under to give the title compound (14.8 g, 100% yield) as a white solid. δH (500 MHz, DMSO) 8.45 (2H, d), 8.02 (2H, d), 3.66-3.54 (5H, m), 2.52 (2H, obscured), 2.45-2.36 (1H, m), 1.96-1.88 (2H, m), 1.64-1.52 (2H, m). Tr=1.88 min m/z (ES+) (M+H+) 329.

Workup

  1. filtrationAfter this time, the resulting solid precipitate was collected by filtration
  2. washwashed with cold THF (50 ml)
  3. custombefore being dried under

Sources & evidence

ORD record
ord-0d6196885ef244cf870f1a7e27f7bf18
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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