Diisopropylethylamine → 3-(Dimethylaminomethylene)-dihydrobenzo[b]pyran-2,4-dione

HRID 1646208Notes

Reaction equation

HRID 1646208 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[CH3:13][N:14]([CH:16]=O)[CH3:15].COS(OC)(=O)=O.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:13][N:14]([CH:16]=[C:3]1[C:4](=[O:12])[O:5][C:6]2=[CH:7][CH:8]=[CH:9][CH2:10][CH:11]2[C:2]1=[O:1])[CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11127270DMF dimethylsulfateHCID 546829304-Hydroxycoumarin

Product 1

HCID 678768173-(Dimethylaminomethylene)-dihydrobenzo[b]pyran-2,4-dioneYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared by the method of example 2, by stirring 4-hydroxycoumarin (5.0 g) and DMF-dimethylsulfate (10.0 g) with ethyldiisopropylamine (10 mL) in CH2Cl2 (100 mL) for 0.5 hour. Product was crystallized from ether-CH2Cl2 to obtain 3.01 g of tan crystals, mp 135°-140° with decomposition.

Workup

  1. customThis compound was prepared by the method of example 2
  2. customProduct was crystallized from ether-CH2Cl2

Sources & evidence

ORD record
ord-6b5a6a04cb284081934a69c3238507d0
Source dataset
uspto-grants-1993_01
Patent number
US05179093

Reaction notes

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