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Triethylamine → 1,4-Bis(6-chloropyridin-3-yl)butane-1,4-diyl dimethanesulfonate

HRID 2364880
Notes
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Reaction equation

HRID 2364880 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:20])[CH2:9][CH2:10][CH:11]([C:13]2[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[OH:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:28][S:29]([O:20][CH:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH:11]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[C:13]1[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1)(=[O:31])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 596171711,4-Bis(6-chloropyridin-3-yl)butane-1,4-diol

Product 1

HCID 596169941,4-Bis(6-chloropyridin-3-yl)butane-1,4-diyl dimethanesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

The product from Example 207B (2.23 g, 7.12 mmol) and triethylamine (2.98 mL, 21.36 mmol) were combined in dichloromethane (50 mL). The mixture was cooled to −20° C. and methanesulfonyl chloride (1.383 mL, 17.80 mmol) was added. The mixture was stirred at room temperature for 1 hour. The solvent was evaporated to give the title product (approx 3.34 g) which was directly used for the next reaction.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-04c6c3a4e929494b9bd18d0202a209bb
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691938B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes