Hydrochloric Acid → HCID 45357346, compound

HRID 1764745Notes

Reaction equation

HRID 1764745 reaction equation
[ClH:1].[N+:2]([CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[N+:13]([O-])=O)=[O:7])([O-])=O>C(O)C>[ClH:1].[ClH:1].[NH2:2][CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[NH2:13])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 120150941-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethan-1-one

Product 1

HCID 45357346HCID 45357346, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 38 g. of stannous chloride dihydrate in 100 ml. of concentrated hydrochloric acid is treated portionwise with 10 g. of 2-nitro-1-[5-nitro-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone. Ten ml. of ethanol are added to clarify the solution and the mixture is stirred at 60° C. for 3 hours. The solution is evaporated to near dryness and three 100 ml. portions of ethanol are added sequentially and evaporated from the residue. The residual syrup is stirred with 800 ml. of ether and the resulting solid is collected by filtration, washed with ether and dried at reduced pressure. This solid (a tin complex) is dissolved in 150 ml. of water and the tin is precipitated as the sulfide by bubbling hydrogen sulfide gas into the solution. The mixture is filtered and the filter cake washed with water. The filtrate and washings are combined and evaporated at reduced pressure. The residue is repeatedly evaporated with 100 ml. portions of ethanol. The final residual gum is triturated with 30 ml. of ethanol to give as a crystalline solid 2-amino-1-[5-amino-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone dihydrochloride, which is collected by filtration, washed with ethanol and dried at reduced pressure; m.p. 155° C. (dec.).

Workup

  1. customThe solution is evaporated
  2. additionportions of ethanol are added sequentially
  3. customevaporated from the residue
  4. stirringThe residual syrup is stirred with 800 ml
  5. filtrationof ether and the resulting solid is collected by filtration
  6. washwashed with ether
  7. customdried at reduced pressure
  8. dissolutionThis solid (a tin complex) is dissolved in 150 ml
  9. customof water and the tin is precipitated as the sulfide
  10. customby bubbling hydrogen sulfide gas into the solution
  11. filtrationThe mixture is filtered
  12. washthe filter cake washed with water
  13. customevaporated at reduced pressure
  14. customThe residue is repeatedly evaporated with 100 ml
  15. customThe final residual gum is triturated with 30 ml

Sources & evidence

ORD record
ord-887c371247f64e8ca4d466b25cc84326
Source dataset
uspto-grants-1978_09
Patent number
US04117229

Reaction notes

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