Triethylamine → 1,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diyl dimethanesulfonate

HRID 2364783Notes

Reaction equation

HRID 2364783 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)[OH:12])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH3:34][S:35]([O:12][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)[CH2:10][CH2:9][CH:8]([O:23][S:35]([CH3:34])(=[O:37])=[O:36])[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 767088951,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diol

Product 1

HCID 767087941,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diyl dimethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 28B (4.81 g, 11.99 mmol) and triethylamine (5.85 mL, 42.0 mmol) were dissolved in dichloromethane (80 mL) at room temperature and treated with methanesulfonyl chloride (2.34 mL, 30.0 mmol) dropwise over 10 minutes. The resulting solution was stirred for 2 h then concentrated to dryness and used directly in the next step.

Workup

  1. concentrationthen concentrated to dryness

Sources & evidence

ORD record
ord-3100ab8d86784bd8a53cef71a9d0a7ea
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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