Acetic Anhydride → HCID 54497139, compound

HRID 1935456Notes

Reaction equation

HRID 1935456 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)C.[NH2:8][C:9]1[S:18][C:12]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:11]=2[C:10]=1[C:19]#[N:20]>C(OCC)(OCC)OCC>[CH2:5]([O:4][CH:1]=[N:8][C:9]1[S:18][C:12]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:11]=2[C:10]=1[C:19]#[N:20])[CH3:6]

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

3.5 ml of acetic anhydride were added to 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 and the mixture was boiled under nitrogen and at reflux for 4 h. After that, the mixture was filtered off with suction, in the hot, through a suction filter and the filtrate was evaporated right down at 80° C. on a rotary evaporator. The residue was taken up in 300 ml of methyl t-butyl ether and this mixture was heated to boiling. After the insoluble solids had been filtered off with suction, 45.4 g (77%) of the product crystallized out in an icebath with stirring. A further 1.7 g (3%) of product were obtained from the mother liquor as a second fraction. m.p.: 88-89° C.

Workup

  1. temperatureat reflux for 4 h
  2. filtrationAfter that, the mixture was filtered off with suction
  3. filtrationin the hot, through a suction filter
  4. customthe filtrate was evaporated right down at 80° C. on a rotary evaporator
  5. temperaturethis mixture was heated to boiling
  6. filtrationAfter the insoluble solids had been filtered off with suction, 45.4 g (77%) of the product
  7. customcrystallized out in an icebath

Sources & evidence

ORD record
ord-8355efd1364c44a3b3f719a5062126a5
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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