2-Nitrobenzenesulfonyl chloride → HCID 68863340, compound

HRID 1725976Notes

Reaction equation

HRID 1725976 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17]>N1C=CC=CC=1>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 11521576HCID 11521576, compound

Product 1

HCID 68863340HCID 68863340, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 418A (4.74 g, 23.09 mmol) in pyridine (46 mL) was treated with 2-nitrobenzenesulfonyl chloride (5.37 g, 24.25 mmol), stirred 24 hours, concentrated, diluted with ethyl acetate (150 mL), washed with 1N HCl (2×100 mL) and brine (100 mL), dried (MgSO4), filtered, and concentrated. The residue was purified by column chromatography (3:1 hexanes/ethyl acetate) to provide the desired product (5.93 g, 66%). MS (ESI(+)) m/e 408 (M+NH4)+; MS (ESI(−)) m/e 389 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.01 (s, 1H), 7.98 (d, 1H), 7.87 (m, 1H), 7.81 (m, 2H), 7.12 (d, 1H), 6.92 (d, 1H), 3.60 (s, 3H), 2.70 (m, 2H), 2.53 (m, 2H), 1.67 (m, 4H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate (150 mL)
  3. washwashed with 1N HCl (2×100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-bdc7b55b27d74ce98a2e98313c37a834
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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