Hydrochloric Acid → HCID 21445649, compound

HRID 1729861Notes

Reaction equation

HRID 1729861 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH2:11][CH2:10][N:9]2[CH2:12][CH:13]([C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[NH:18][CH:19]=O)[N:14]=[C:8]12.[OH-].[Na+].[ClH:26]>CO.O.O1CCCC1>[ClH:26].[ClH:26].[CH3:19][NH:18][C:17]1[CH:16]=[C:15]([CH:13]2[CH2:12][N:9]3[C:8]([S:7][CH2:11][CH2:10]3)=[N:14]2)[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12850509HCID 12850509, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21445649HCID 21445649, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred slurry of 1.15 g. (0.030 mole) of lithium aluminum hydride in 80 ml. of dry tetrahydrofuran is added 5.00 g. (0.0203 mole) of 3'-(2,3,5,6-tetrahydroimidazo[2,1-b]thiazol-6-yl)formanilide (Example 12) at a rate sufficient to keep the temperature at 40°-45°C. The reaction mixture is then stirred at room temperature for 3 hours and at 40°-50°C. for 30 minutes. After cooling the reaction, 1.8 ml. of water is cautiously added dropwise and then 2 ml. of 15% aqueous sodium hydroxide. The mixture is filtered and the filter cake washed with tetrahydrofuran. Evaporation of the solvent gives an oil which is dissolved in methanol and acidified with 2-propanolic hydrogen chloride. Filtration of the precipitate gives 4.18 g. (67% yield) of crude product which is recrystallized from methanol and has melting point 229°-231°C. Anal. Calcd. for C12H16N3SCl: C, 47.06; H, 5.60; N, 13.72; S, 10.47; Cl, 23.15. Found: C, 46.82; H, 5.56; N, 13.60; S, 10.40; Cl, 23.16.

Workup

  1. customat 40°-45°C
  2. temperatureAfter cooling
  3. customthe reaction, 1.8 ml
  4. filtrationThe mixture is filtered
  5. washthe filter cake washed with tetrahydrofuran
  6. customEvaporation of the solvent
  7. customgives an oil which
  8. filtrationFiltration of the precipitate
  9. customgives 4.18 g

Sources & evidence

ORD record
ord-701138d6003a4025b59f268c700762bd
Source dataset
uspto-grants-1976_11
Patent number
US03989835

Reaction notes

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