Methane → HCID 20190395, compound

HRID 1788769Notes

Reaction equation

HRID 1788769 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C(N(CC)CC)C.Cl.Cl[C:19]([C:21]1[CH:22]=[C:23]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[N:24]2[C:28]=1[CH2:27][S:26][CH2:25]2)=[O:20].C>C(Cl)Cl.C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:19]([C:21]2[CH:22]=[C:23]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[N:24]3[C:28]=2[CH2:27][S:26][CH2:25]3)=[O:20])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 20190397HCID 20190397, compound

Product 1

HCID 20190395HCID 20190395, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 3-methoxyaniline (3.1 g) and of triethylamine (5.1 g) in methylene chloride (50 cc) is added over 15 minutes at a temperature of between 21° and 28° C. to a suspension of 7-chloroformyl-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (7.5 g) in methylene chloride (125 cc). The solution obtained is stirred at a temperature of about 20° C. for 16 hours. A product precipitates out. The crystals which have appeared are separated off by filtration, washed 3 times with methylene chloride (300 cc in total) and 3 times with distilled water (300 cc in total) and then 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 (5.1 g) melting at 220° C. is thus obtained. This product is dissolved in boiling 1-butanol (160 cc). The cloudy solution obtained is treated with decolourising charcoal (0.5 g) and filtered hot. The filtrate is cooled at a temperature of about 4° C. for 16 hours. The crystals which have appeared are separated off by filtration, washed twice with 1-butanol (30 cc in total) 3 times with ethanol (75 cc in total) and 3 times with diethyl ether (75 cc in total) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. N-(3-Methoxyphenyl)-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (3.9 g) is thus obtained in the form of pale yellow crystals melting at 224° C.

Workup

  1. customThe solution obtained
  2. customA product precipitates out
  3. customThe crystals which have appeared are separated off by filtration
  4. washwashed 3 times with methylene chloride (300 cc in total) and 3 times with distilled water (300 cc in total)
  5. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets
  6. customA crude product (5.1 g) melting at 220° C. is thus obtained
  7. dissolutionThis product is dissolved
  8. customThe cloudy solution obtained
  9. filtrationfiltered hot
  10. temperatureThe filtrate is cooled at a temperature of about 4° C. for 16 hours
  11. customThe crystals which have appeared are separated off by filtration
  12. washwashed twice with 1-butanol (30 cc in total) 3 times with ethanol (75 cc in total) and 3 times with diethyl ether (75 cc in total)
  13. dry with materialdried 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-a74cdf5f7cf24cd5b1c5653175416195
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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