Hydrogen Sulfide → Methyl p-[2-(p-amidinobenzamido)ethyl]phenoxyacetate

HRID 1609009Notes

Reaction equation

HRID 1609009 reaction equation
S.[C:2]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[O:9])=[CH:6][CH:5]=1)#[N:3].[N:27]1C=CC=CC=1.C(N(CC)CC)C>>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[O:9])=[CH:25][CH:26]=1)(=[NH:27])[NH2:3]

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 10315069Methyl 4-[2-(p-cyanobenzamido)ethyl]phenoxyacetateHCID 22561186Pyridine triethylamine

Product 1

HCID 10360837Methyl p-[2-(p-amidinobenzamido)ethyl]phenoxyacetate

Procedure

H2S was passed for 45 minutes through a suspension of 2.0 g of methyl 4-[2-(p-cyanobenzamido)ethyl]phenoxyacetate in 24 ml of pyridine/triethylamine (7:1) at 0° C. The solution resulting after 12 hours was concentrated, and a suspension was made of the residue in methanol and filtered. The residue on the filter was immediately suspended in 30 ml of acetone, and 4 ml of methyl iodide were added. After 2.5 hours the precipitate was filtered off, washed with a little acetone and, after drying, dissolved in 20 ml of methanol. 2.0 g of ammonium acetate were added and the mixture was then left to react at room temperature for 2 hours, during which a colorless precipitate formed, and this was filtered off and reprecipitated from methanol. Methyl p-[2-(p-amidinobenzamido)ethyl]phenoxyacetate was obtained as the acetate salt, melting point above 200° C., after drying under high vacuum.

Workup

  1. customThe solution resulting after 12 hours
  2. concentrationwas concentrated
  3. filtrationfiltered
  4. addition4 ml of methyl iodide were added
  5. filtrationAfter 2.5 hours the precipitate was filtered off
  6. washwashed with a little acetone
  7. customafter drying
  8. dissolutiondissolved in 20 ml of methanol
  9. addition2.0 g of ammonium acetate were added
  10. waitthe mixture was then left
  11. customto react at room temperature for 2 hours, during which a colorless precipitate
  12. customformed
  13. filtrationthis was filtered off
  14. customreprecipitated from methanol

Sources & evidence

ORD record
ord-8d1a93a08dcb4d0b96b756ad1ec4c9a2
Source dataset
uspto-grants-1995_03
Patent number
US05399585

Reaction notes

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