Water → HCID 131729544, compound

HRID 1686470Notes

Reaction equation

HRID 1686470 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:31])[CH2:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[CH:21][C:20]=2[Cl:30])[CH:12]=1.Cl.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]Cl.O>CN(C=O)C>[CH3:7][O:8][C:9](=[O:31])[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])[CH:14]=[C:13]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[CH:21][C:20]=2[Cl:30])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 131729542HCID 131729542, compound

Product 1

HCID 131729544HCID 131729544, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.46 g) was added to a solution of the product from step (i) (1.10 mmol) and 2-dimethylamino ethyl chloride hydrochloride (0.16 g) in DMF at RT. After 1 h no reaction was evident so the mixture was heated to 60° C. for 18 h. Water was added and the mixture extracted with ethyl acetate, washed (brine) and the organics dried (MgSO4) and concentrated to a green oil which was purified by flash column chromatography (eluent 1% triethylamine and 2% methanol in ethyl acetate) to give the subtitle compound as a coulourless oil (100 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washwashed (brine)
  3. dry with materialthe organics dried (MgSO4)
  4. concentrationconcentrated to a green oil which
  5. customwas purified by flash column chromatography (eluent 1% triethylamine and 2% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-ab1e94541fd6497bbe53b37a11813c42
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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