Ethanolamine → HCID 22464549, compound

HRID 1935476Notes

Reaction equation

HRID 1935476 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(O[CH:8]=[N:9][C:10]1[S:18][C:17]2[CH2:16][CH2:15][N:14]([CH2:19][CH3:20])[CH2:13][C:12]=2[C:11]=1[C:21](OCC)=[O:22])C>C(O)C>[OH:2][CH2:1][CH2:3][N:4]1[C:21](=[O:22])[C:11]2[C:12]3[CH2:13][N:14]([CH2:19][CH3:20])[CH2:15][CH2:16][C:17]=3[S:18][C:10]=2[N:9]=[CH:8]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 54376764HCID 54376764, compound

Product 1

HCID 22464549HCID 22464549, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 ml (81 mmol) of ethanolamine were added to 17.0 g (55 mmol) of 2-ethoxymethyleneamino-3-carboethoxy-5-ethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine in 130 ml of ethanol, and the mixture was boiled at reflux for 2 h. The mixture was then evaporated down to a volume of approx. 50 ml and this was thoroughly stirred in an ice bath. The fine solids which precipitated out were filtered off with suction and then washed with cold ethyl acetate. 10.5 g (63%) of a pale brown product were isolated.

Workup

  1. temperatureat reflux for 2 h
  2. customThe mixture was then evaporated down to a volume of approx. 50 ml
  3. customThe fine solids which precipitated out
  4. filtrationwere filtered off with suction
  5. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-1f537f56aab44071a02c31e25ed1e795
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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