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

HRID 1470924Notes

Reaction equation

HRID 1470924 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-52f291a38f054179a5a611d7af64ff58
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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