4-Toluenesulfonyl chloride → 3,3'-Methylenebis[4-tosylcoumarin]

HRID 48530Notes

Reaction equation

HRID 48530 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:11][C:9](=[O:10])[C:8]([CH2:12][C:13]3[C:22](=[O:23])[O:21][C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:14]=3O)=[C:7](O)[C:5]=2[CH:6]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl.C(N(CC)CC)C>[CH2:12]([C:8]1[C:9](=[O:10])[O:11][C:4]2[C:3]([C:7]=1[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33])=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:13]1[C:22](=[O:23])[O:21][C:20]2[C:15]([C:14]=1[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33])=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 54676038Dicoumarol

Product 1

HCID 227434643,3'-Methylenebis[4-tosylcoumarin]

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of dicumarol (10 mmol) and p-toluenesulfonyl chloride (1.0 eq.) in dichloromethane (20 ml), triethylamine was added at room temperature under air atmosphere. After the reaction was complete, as monitored by TLC, the reaction mixture was evaporated and the residue was purified by flash chromatography (silica gel) to afford the product, 3,3′-methylenebis[4-tosylcoumarin].

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-ff7263e56b6c4ca5a56104dfac33b28b
Source dataset
uspto-grants-2004_03
Patent number
US06703514B2

Reaction notes

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