Hydrochloric Acid → HCID 178478805, compound

HRID 280741Notes

Reaction equation

HRID 280741 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[N:8]=[C:9]([NH:12][C:13]([NH2:15])=[NH:14])[S:10][CH:11]=1)=[O:6])=[N+]=[N-].C(O)C.[ClH:19]>[Pd].O>[ClH:19].[ClH:19].[NH2:1][CH2:4][C:5]([C:7]1[N:8]=[C:9]([NH:12][C:13]([NH2:15])=[NH:14])[S:10][CH:11]=1)=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178514602HCID 178514602, compound

Product 1

HCID 178478805HCID 178478805, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 962WaterSolvent3×

Procedure

A mixture of 12.0 g (53 mmol) of 2-azido-1-(2-guanidino-4-thiazolyl)ethanone, 1.0 g of 10% palladium on carbon, 100 ml of ethanol, 50 ml of water, and 20 ml of concentrated hydrochloric acid was hydrogenated at 3 atm. and room temperature for 1 hour. At this point another 50 ml of water and 300 mg of 10% palladium on carbon was added to the mixture and hydrogenation was continued at 3 atm for another 0.75 hour. The mixture was diluted with 200 ml of water, filtered to remove the catalyst, and the filtrate concentrated leaving 13.1 g (92%) of 2-amino-1-(2- guanidino-4-thiazolyl)ethanone dihydrochloride as a white powder mp >270°. nmr (DMSO-d6) (δ): 8.58 (b, 4H) 8.44 (s, 1H); 4.58 (b, 4H).

Workup

  1. waitwas continued at 3 atm for another 0.75 hour
  2. filtrationfiltered
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-fb36e93ec4484ec4aab4f683355766df
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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