Dimethylformamide → Hydrochloric Acid

HRID 1979914Notes

Reaction equation

HRID 1979914 reaction equation
CCCCC.[H-].[Na+].[ClH:8].[NH:9]1[CH2:13][CH2:12][N:11]=[CH:10]1.[Cl:14][C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][N:20]=1.CN(C)[CH:26]=[O:27]>C(OCC)C>[ClH:14].[OH2:27].[ClH:8].[ClH:14].[NH:11]1[CH2:12][CH2:13][N:9]=[C:10]1[CH2:26][O:27][C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][N:20]=1.[NH:11]1[CH2:12][CH2:13][N:9]=[C:10]1[CH2:26][O:27][C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][N:20]=1.[ClH:14].[ClH:14]

Participants

8

Reactant 5

HCID 6228Dimethylformamide2×HCID 8003PentaneHCID 24758Sodium hydrideHCID 2148131H-Imidazole, 4,5-dihydro-, monohydrochlorideHCID 102612868-Chloroimidazo[1,2-a]pyrazine

Product 2

HCID 313Hydrochloric AcidHCID 70515829HCID 70515829, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a slurry of 530 mg (22 mmol) of pentane-washed sodium hydride in 50 ml of dry dimethylformamide (DMF) was added 1.37 g (10.0 mmol) of 2-hydroxymethyl)-4,5-dihydroimidazole hydrochloride. After 30 minutes at room temperature, 1.55 g (10.0 mmol) of 8-chloroimidazo[1,2-a]pyrazine in 30 ml of DMF was added dropwise. After 1 hour at room temperature, the mixture was concentrated to dryness. The residue was dissolved in 30 ml of water and extracted with 2×50 ml of chloroform. The combined organic extracts were dried (Na2SO4), filtered, and concentrated. The oily residue was purified by flash chromatography (230-400 mesh SiO2 ; 10% MeOH/CHCl3 saturated with NH3 as eluent) to afford the product. Treatment with ethanolic HCl and excess diethyl ether afforded the crystalline dihydrochloride hemihydrate salt of the product, m.p. 162°-165° C. (dec).

Workup

  1. waitAfter 1 hour at room temperature
  2. concentrationthe mixture was concentrated to dryness
  3. dissolutionThe residue was dissolved in 30 ml of water
  4. extractionextracted with 2×50 ml of chloroform
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily residue was purified by flash chromatography (230-400 mesh SiO2 ; 10% MeOH/CHCl3 saturated with NH3 as eluent)
  9. customto afford the product

Sources & evidence

ORD record
ord-710eac6131d545088e54ef9e107c6e55
Source dataset
uspto-grants-1984_11
Patent number
US04483858

Reaction notes

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