Methane → HCID 13375488, compound

HRID 1788761Notes

Reaction equation

HRID 1788761 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]3[CH2:12][S:13][CH2:14][C:10]3=[C:9]([C:15]#[N:16])[CH:8]=2)[CH:2]=1.[OH-].[K+].C([OH:21])C.C>C(O)(C)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]3[CH2:12][S:13][CH2:14][C:10]3=[C:9]([C:15]([NH2:16])=[O:21])[CH:8]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 702EthanolHCID 14797Potassium HydroxideHCID 13375482HCID 13375482, compound

Product 1

HCID 13375488HCID 13375488, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carbonitrile (11.35 g) and of potassium hydroxide powder (14 g) in tert-butyl alcohol (100 cc) is heated at 85° C. for 1 hour. After 16 hours' stirring at a temperature of about 20° C., the reaction mixture is poured into distilled water (2 liters). The suspension is stirred at a temperature of about 20° C. for 15 minutes and then the crystals which have appeared are separated off by filtration, washed 8 times with distilled water (1,200 cc in total) and then 3 times with ethanol (150 cc in total) and are dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. A crude product (10.5 g) is thus obtained which is combined with a product (3.9 g) prepared in the same manner in an earlier operation and dissolved in boiling ethanol (850 cc). The solution is treated with decolourising charcoal (0.5 g) and filtered hot. The filtrate is cooled at a temperature of about 4° C. for 3 days. The crystals which have appeared are separated off by filtration, washed 3 times with ethanol (30 cc in total) cooled to a temperature of about 4° C. and are dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. 5-(3-Pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (11.3 g) is thus obtained in the form of cream crystals melting at 215° C.

Workup

  1. additionthe reaction mixture is poured
  2. distillationinto distilled water (2 liters)
  3. stirringThe suspension is stirred at a temperature of about 20° C. for 15 minutes
  4. customthe crystals which have appeared are separated off by filtration
  5. washwashed 8 times with distilled water (1,200 cc in total)
  6. dry with material3 times with ethanol (150 cc in total) and are dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets
  7. customA crude product (10.5 g) is thus obtained which
  8. customprepared in the same manner in an earlier operation
  9. dissolutiondissolved
  10. filtrationfiltered hot
  11. temperatureThe filtrate is cooled at a temperature of about 4° C. for 3 days
  12. customThe crystals which have appeared are separated off by filtration
  13. washwashed 3 times with ethanol (30 cc in total)
  14. temperaturecooled to a temperature of about 4° C.
  15. dry with materialare dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-2dfe2c76b5b841aea8d11b048080f5c7
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

Loading…