Trifluoroacetic acid → HCID 20154010, compound

HRID 364124Notes

Reaction equation

HRID 364124 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[S:9][CH2:8][C:7](=O)[CH2:6]2.[CH2:14]([NH:17][CH2:18][CH2:19][C:20](OC)=[O:21])[CH2:15][CH3:16].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[S:9][CH2:8][C:7]3[N:17]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19][C:20](=[O:21])[C:6]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 10630640HCID 10630640, compoundHCID 20154025HCID 20154025, compound

Product 1

HCID 20154010HCID 20154010, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The starting material is prepared as follows: A mixture of 7.5 g 6-methoxythiochroman-3-one [J. Org. Chem. 34, 1566 (1969)], 5.8 g of methyl 3-(propylamino)-propionate and 0.8 ml of trifluoroacetic acid in 80 ml of toluene is heated under reflux for 22 hours in a Dean Stark apparatus. Additional 0.8 ml portions of trifluoroacetic acid are added after 2, 5, and 16 hours. The solvent is removed, the residue is taken up in ether and the product is extracted with 3N hydrochlorid acid. After neutralization the aqueous layers are extracted with ethyl acetate, the organic layer is dried and the solvent is removed. The product is crystallized from a small volume of methanol to afford 9-methoxy-4-propyl-1,2,3,5-tetrahydro-4H-[1]-benzothiopyrano[3,4-b]pyridin-1-one, m.p. 108°-110°.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated
  3. temperatureunder reflux for 22 hours in a Dean Stark apparatus
  4. customThe solvent is removed
  5. extractionthe product is extracted with 3N hydrochlorid acid
  6. extractionAfter neutralization the aqueous layers are extracted with ethyl acetate
  7. customthe organic layer is dried
  8. customthe solvent is removed
  9. customThe product is crystallized from a small volume of methanol

Sources & evidence

ORD record
ord-f3fe596c13e54c37bfeeb77c9a2c4e9f
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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