Acetic Acid → 1-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione

HRID 362564

Reaction equation

HRID 362564 reaction equation
Cl[C:2]1[C:7]2[N:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=[CH:4][N:3]=1.O.[SH2:13].[Na].O.C(O)(=O)C>CN(C)C=O>[CH3:11][N:10]1[C:6]2[CH:5]=[CH:4][NH:3][C:2](=[S:13])[C:7]=2[N:8]=[CH:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 9487924-chloro-1-methyl-1H-imidazo(4,5-c)pyridineHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 193535981-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thioneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

4.00 g (23.9 mmol) of 4-chloro-1-methyl-1H-imidazo[4,5-c]pyridine in 27 ml of dimethylformamide were stirred at 115° C. for 18 hours with 8.10 g (95.6 mmol) of sodium hydrogen sulphide hydrate. After cooling the mixture was treated with 110 ml of water, adjusted to pH 4 with acetic acid and stirred at 5° C. while cooling with ice for 15 min. The precipitate was filtered off and washed with water. After drying there were obtained 3.73 g (95%) of 1-methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione as white crystals with m.p. >300° C.

Workup

  1. temperatureAfter cooling the mixture
  2. temperaturewhile cooling with ice for 15 min
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customAfter drying there

Sources & evidence

ORD record
ord-505a70ca758b4c6cae28240203f97f47
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Linked notes

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