Acetic Anhydride → HCID 54497139, compound

HRID 325069Notes

Reaction equation

HRID 325069 reaction equation
[NH2:1][C:2]1[S:11][C:5]2[CH2:6][N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:12]#[N:13].[C:14]([O:17][C:18](=O)C)(=O)[CH3:15]>C(OCC)(OCC)OCC>[CH2:14]([O:17][CH:18]=[N:1][C:2]1[S:11][C:5]2[CH2:6][N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:12]#[N:13])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2642962-Amino-6-methyl-4,5,6,7-tetrahydrothieno(2,3-c)pyridine-3-carbonitrile

Product 1

HCID 54497139HCID 54497139, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

46.0 g (238 mmol) of 2-amino-3-cyano-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine in 250 ml of triethyl orthoformate were mixed with 3.5 ml of acetic anhydride and refluxed under nitrogen for 4 h. The mixture was then filtered hot under suction, and the filtrate was completely evaporated in a rotary evaporator at 80° C. The residue was taken up in 300 ml of methyl t-butyl ether and heated to boiling. After removal of the insoluble solids by filtration with suction, 45.4 g (77%) of product crystallized on stirring in an ice bath. 1.7 g (3%) of product were obtained as second fraction from the mother liquor. Melting point: 88-89° C.

Workup

  1. temperaturerefluxed under nitrogen for 4 h
  2. filtrationThe mixture was then filtered hot under suction
  3. customthe filtrate was completely evaporated in a rotary evaporator at 80° C
  4. temperatureheated to boiling
  5. customAfter removal of the insoluble solids
  6. filtrationby filtration with suction, 45.4 g (77%) of product
  7. customcrystallized

Sources & evidence

ORD record
ord-3c150581ce1c49f6a4fdd7f88bcf831f
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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