Ethanolamine → HCID 15453507, compound

HRID 325074Notes

Reaction equation

HRID 325074 reaction equation
C(O[CH:4]=[N:5][C:6]1[S:15][C:9]2[CH2:10][N:11]([CH3:14])[CH2:12][CH2:13][C:8]=2[C:7]=1[C:16]([O:18]CC)=O)C.[CH2:21]([CH2:23][NH2:24])[OH:22]>C(O)C>[OH:22][CH2:21][CH2:23][N:24]1[C:16](=[O:18])[C:7]2[C:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][C:9]=3[S:15][C:6]=2[N:5]=[CH:4]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 54312022HCID 54312022, compound

Product 1

HCID 15453507HCID 15453507, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

86.4 g (292 mmol) of 2-ethoxymethyleneamino-3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine in 200 ml of ethanol were mixed with 17.6 ml (292 mmol) of ethanolamine and refluxed for 2 h. The mixture was then concentrated under reduced pressure, and the residue was taken up in 30 ml of ethyl acetate with stirring. The solid which precipitated overnight was filtered off with suction and washed with a little ethyl acetate. After recrystallization from ethanol, 48.0 g (62%) of product with melting point 163-165° C. were isolated.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customThe solid which precipitated overnight
  4. filtrationwas filtered off with suction
  5. washwashed with a little ethyl acetate
  6. customAfter recrystallization from ethanol, 48.0 g (62%) of product with melting point 163-165° C.
  7. customwere isolated

Sources & evidence

ORD record
ord-b0eac9f4b4d24a4c8a482810d9f8c7ff
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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