Triethylamine → HCID 19084626, compound

HRID 864660Notes

Reaction equation

HRID 864660 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](O)[CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1.C(N(CC)CC)C.[CH3:29][N:30]=[C:31]=[O:32]>CN(C)C=O>[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]([C:31](=[O:32])[NH:30][CH3:29])[CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 11067259HCID 11067259, compound

Product 1

HCID 19084626HCID 19084626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2,6-dichlorophenoxy)-6-hydroxycoumarin (0.5 g, 1.55 mmole) in dimethyl formamide, under nitrogen, at room temperature is treated with triethylamine (0.7 mL, 5 mole), then treated with CH3NCO (0.5 mL, 5.5 mole) and allowed to stir at room temperature for about 1 hour. When the reaction is complete by HPLC analysis, the reaction mixture is poured onto water and extracted with methylene chloride. The extracts are concentrated in vacuo to give a residue. The residue is crystallized from methylene chloride/hexane to afford the title product as white crystals, 0.382 (71% yield), mp 292°-299° C., identified by 1HNMR, 13CNMR and IR analyses.

Workup

  1. additionthe reaction mixture is poured onto water
  2. extractionextracted with methylene chloride
  3. concentrationThe extracts are concentrated in vacuo
  4. customto give a residue
  5. customThe residue is crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-2515135f24d14dc08b04bbf620349257
Source dataset
uspto-grants-1996_10
Patent number
US05563280

Reaction notes

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