Water → HCID 19956256, compound

HRID 1779489Notes

Reaction equation

HRID 1779489 reaction equation
O.Cl.Cl[CH2:4][CH2:5][N:6]([CH3:8])[CH3:7].[OH:9]/[N:10]=[C:11]1/[C:12]2[N:13]([CH:20]=[CH:21][CH:22]=2)[C:14]2[C:18]([CH3:19])=[CH:17][S:16][C:15]/1=2.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH3:7][N:6]([CH2:5][CH2:4][O:9]/[N:10]=[C:11]1/[C:12]2[N:13]([CH:20]=[CH:21][CH:22]=2)[C:14]2[C:18]([CH3:19])=[CH:17][S:16][C:15]/1=2)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 19956241HCID 19956241, compound

Product 1

HCID 19956256HCID 19956256, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.32 g of water and then 3.91 g of 1-chloro-2-(N,N-dimethylamino)ethane hydrochloride and 5 g of (Z)-8-hydroxyimino-3-methylthieno[2,3-d]pyrrolo[1,2-a]pyrrole (Preparation 36) are added to 6.99 g of sodium carbonate in 200 ml of anhydrous acetone. The reaction mixture is heated at reflux for 40 hours, then the acetone is removed and the residue is taken up in 100 ml of water and then extracted with 200 ml of diethyl ether. The ethereal phase is washed with water, decanted off and then dried over magnesium sulfate, and subsequently concentrated to dryness to yield the title product in the form of an oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 40 hours
  3. customthe acetone is removed
  4. extractionextracted with 200 ml of diethyl ether
  5. washThe ethereal phase is washed with water
  6. customdecanted off
  7. dry with materialdried over magnesium sulfate
  8. concentrationsubsequently concentrated to dryness

Sources & evidence

ORD record
ord-746ee4dbe858440b8b08860ae943a481
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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