Dimethylcarbamoyl Chloride → HCID 19966515, compound

HRID 1450514Notes

Reaction equation

HRID 1450514 reaction equation
[CH3:1][C:2]1[O:7][C:6]2[CH:8]=[C:9]3[C:14](=[C:15]([OH:16])[C:5]=2[C:4](=[O:38])[CH:3]=1)[C:13]([OH:17])=[CH:12][C:11]([OH:18])=[C:10]3[C:19]1[C:34]2[C:23](=[C:24]([OH:35])[C:25]3[C:30](=[O:31])[CH:29]=[C:28]([CH3:32])[O:27][C:26]=3[CH:33]=2)[C:22]([OH:36])=[CH:21][C:20]=1[OH:37].[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>N1C=CC=CC=1>[OH:16][C:15]1[C:5]2[C:4](=[O:38])[CH:3]=[C:2]([CH3:1])[O:7][C:6]=2[CH:8]=[C:9]2[C:14]=1[C:13]([OH:17])=[CH:12][C:11]([O:18][C:41]([N:40]([CH3:44])[CH3:39])=[O:42])=[C:10]2[C:19]1[C:34]2[C:23](=[C:24]([OH:35])[C:25]3[C:30](=[O:31])[CH:29]=[C:28]([CH3:32])[O:27][C:26]=3[CH:33]=2)[C:22]([OH:36])=[CH:21][C:20]=1[O:37][C:41]([N:40]([CH3:44])[CH3:39])=[O:42]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 178428879HCID 178428879, compound

Product 1

HCID 19966515HCID 19966515, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 50 mg of 2-methyl-5,6,8-trihydroxy-9-(5,6,8-trihydroxy-2-methyl-4H-naphtho[2,3,b]pyran-4-one-9yl)-4H-naphtho[2,3,b]pyran-4-one in 2 ml of pyridine at 0° C. was added with 0.02 ml of dimethylcarbamoyl chloride. The mixture was then stirred at 0° C. for 2 hours and warmed to room temperature overnight. The mixture was quenched with 1 ml of 0.1N sodium hydroxide solution, stirred for 20 minutes and partitioned between chloroform and water. The chloroform layer was then washed with diluted hydrochloric acid solution, saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated. The resulting solid was purified on HPLC on a C-18 silical gel column to provide the title compound.

Workup

  1. temperaturewarmed to room temperature overnight
  2. customThe mixture was quenched with 1 ml of 0.1N sodium hydroxide solution
  3. stirringstirred for 20 minutes
  4. custompartitioned between chloroform and water
  5. washThe chloroform layer was then washed with diluted hydrochloric acid solution, saturated sodium bicarbonate solution, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was purified on HPLC on a C-18 silical gel column

Sources & evidence

ORD record
ord-6fb1cf162d7e4229bafc360e46363887
Source dataset
uspto-grants-1997_02
Patent number
US05602171

Reaction notes

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