Ethanolamine → HCID 15453507, compound

HRID 1725574Notes

Reaction equation

HRID 1725574 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 mM) 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 mM) of ethanolamine and refluxed for 2 h. The mixture was then concentrated in vacuo, 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 in vacuo
  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-16f3d7aea67b4bfaabd1e4fb401fc92f
Source dataset
uspto-grants-2009_02
Patent number
US07491729B2

Reaction notes

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