Dimethylformamide → HCID 22672848, compound

HRID 1006716Notes

Reaction equation

HRID 1006716 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=2[CH3:26])=[CH:11][C:10]=1[S:27]([OH:30])(=O)=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cs].CN(C=O)C.C(Cl)(=O)C([Cl:40])=O>C(Cl)Cl.CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=2[CH3:26])=[CH:11][C:10]=1[S:27]([Cl:40])(=[O:30])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5354618CesiumHCID 22672852HCID 22672852, compound

Product 1

HCID 22672848HCID 22672848, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of the title D compound, 2-benzyloxy-5-(2,6-dimethyl-4-nitrophenoxy)-benzenesulfonic acid, cesium salt (9.9 g, 20 mmol) in 200 mL of CH2Cl2 is treated with DMF (3.1 mL, 40 mmol), then oxalyl chloride (3.5 mL, 40 mmol) is added over 30 min at RT. The reaction mixture is stirred for 1 h further, then diluted with Et2O (200 mL) and washed with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The product is washed with Et2O (5 mL) and dried in vacuo to afford 2-benzyloxy-5-(2,6-dimethyl-4-nitro-phenoxy)benzenesulfonyl chloride: NMR (CDCl3) 2.24 (s, 6H), 5.31 (s, 2H), 7.02 (dd, 1H, J=8.7, 3.8), 7.10 (d, 1H, J=8.7), 7.32-7.47 (m, 4H), 7.52 (d, 2H, J=7.5), 8.05 (s, 2H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  3. concentrationconcentrated
  4. washThe product is washed with Et2O (5 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-24a198c8dd11462db99d2b8ec198a7f5
Source dataset
uspto-grants-2004_09
Patent number
US06790978B2

Reaction notes

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