Methane → HCID 12939927, compound

HRID 443839Notes

Reaction equation

HRID 443839 reaction equation
O[CH2:2][CH:3]1[N:8]([C:9](=[S:21])[NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)[CH2:7][C:6]2[S:22][CH:23]=[CH:24][C:5]=2[CH2:4]1.C.C(O)(C)C>Cl>[CH:16]1[C:17]2[C:12](=[C:11]([N:10]=[C:9]3[N:8]4[CH2:7][C:6]5[S:22][CH:23]=[CH:24][C:5]=5[CH2:4][CH:3]4[CH2:2][S:21]3)[CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 3776IsopropanolHCID 12939923HCID 12939923, compound

Product 1

HCID 12939927HCID 12939927, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of (RS)-5-hydroxymethyl-6-[(isoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (21 g) in 6 N hydrochloric acid (220 cc) is heated under reflux for 1.5 hours. The resulting brown solution is cooled, decolorised with animal charcoal and filtered. The filtrate is rendered alkaline to pH 11 with a 15% aqueous solution of potassium carbonate and extracted with methylene chloride (300 cc and then 3×200 cc). The organic extracts are combined and dried over sodium sulphate. After filtering and concentrating the filtrate to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C., a pale yellow solid is obtained. This solid is dissolved in boiling isopropanol (800 cc); the resulting solution is cooled to +5° C. and kept at that temperature for 20 hours. The solid formed is filtered off and taken up in boiling isopropanol (500 cc); the resulting solution is cooled to +5° C. and kept at that temperature for 20 hours. The solid formed is filtered off, washed with diisopropyl ether (2×50 cc) and dried at 60° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)-7-[(Isoquinol-5-yl)imino]-4,4a,5,9-tetrahydrothiazolo[3,4-a]thieno[3,2-d]pyridine (13.9 g) is thus obtained in the form of pale yellow crystals melting at 171° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe resulting brown solution is cooled
  4. filtrationfiltered
  5. extractionextracted with methylene chloride (300 cc
  6. dry with materialdried over sodium sulphate
  7. filtrationAfter filtering
  8. concentrationconcentrating the filtrate to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C.
  9. customa pale yellow solid is obtained
  10. dissolutionThis solid is dissolved
  11. temperaturethe resulting solution is cooled to +5° C.
  12. customThe solid formed
  13. filtrationis filtered off
  14. temperaturethe resulting solution is cooled to +5° C.
  15. waitkept at that temperature for 20 hours
  16. customThe solid formed
  17. filtrationis filtered off
  18. washwashed with diisopropyl ether (2×50 cc)
  19. customdried at 60° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-53510988601b4b769ba6f621bdc29851
Source dataset
uspto-grants-1981_04
Patent number
US04261999

Reaction notes

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