Dimethylformamide → HCID 19084625, compound

HRID 864661Notes

Reaction equation

HRID 864661 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1.[CH3:22][O:23][CH2:24]OC.O=P(Cl)(Cl)Cl.CN(C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:22][O:23][CH3:24])[CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8020DimethoxymethaneHCID 24813Phosphorus oxychlorideHCID 11067259HCID 11067259, compound

Product 1

HCID 19084625HCID 19084625, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(2,6-dichlorophenoxy)-6-hydroxycoumarin (1.2 g, 3.2 mmole), dimethoxymethane (0.565 g, 7.4 mmole), POCl3 (0.74 g, 4.8 mmole) and dimethylformamide (0.43 g, 5.94 mmole) in toluene is heated at 90°-100° C. for 4 hours, cooled to room temperature, poured onto ice water and filtered. The filtercake is dried and recrystallized from acetonitrile/water to afford the title product, 0.45 g (38% yield), mp 302°-305° C. (dec), identified by 1HNMR, 13CNMR and IR analyses.

Workup

  1. temperatureis heated at 90°-100° C. for 4 hours
  2. additionpoured onto ice water
  3. filtrationfiltered
  4. customThe filtercake is dried
  5. customrecrystallized from acetonitrile/water

Sources & evidence

ORD record
ord-780781fab3b54197aef60f3d02fd7e45
Source dataset
uspto-grants-1996_10
Patent number
US05563280

Reaction notes

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