Ethanolamine → HCID 59473782, compound

HRID 2069729Notes

Reaction equation

HRID 2069729 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C(=O)(O)[O-].[Na+].[C:16](Cl)(Cl)=[S:17].[CH2:20]([CH2:22][NH2:23])[OH:21]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:16]([NH:23][CH2:22][CH2:20][OH:21])=[S:17])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 59473782HCID 59473782, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-bromo-3-amino-1-methyl-2-pyridone (500 mg, 2.46 mmol) in chloroform (12 mL) was added a solution of saturated aqueous sodium bicarbonate (12 mL). To the vigorously stirred mixture was added thiophosgene (0.2 mL, 2.7 mmol) via drop-wise addition. The mixture was stirred for 1 hour and then transferred to a separatory funnel. The chloroform phase was collected and the aqueous phase was back extracted with methylene chloride (10 mL). The organic phases were combined in a 100 mL round bottom flask. To the rapidly stirred solution was added ethanolamine (0.16 mL, 2.7 mmol) via slow drop-wise addition. The material was stirred for 1.5 hours and the precipitated product was collected by filtration. The solid was dried in a vacuum oven providing the desired product as a light white-yellow solid (515 mg). (M−H)−=304/306 m/e.

Workup

  1. additionvia drop-wise addition
  2. customtransferred to a separatory funnel
  3. customThe chloroform phase was collected
  4. extractionthe aqueous phase was back extracted with methylene chloride (10 mL)
  5. customThe organic phases were combined in a 100 mL round bottom flask
  6. additionvia slow drop-wise addition
  7. stirringThe material was stirred for 1.5 hours
  8. filtrationthe precipitated product was collected by filtration
  9. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-5df9ce9274284ecca99ae7e3c5070e79
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…