Sulfamide → HCID 178512633, compound

HRID 894314Notes

Reaction equation

HRID 894314 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[NH:17])OC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[S:18]([NH2:22])([NH2:21])(=[O:20])=[O:19]>CO>[S:18]([NH:22][C:14](=[NH:17])[CH2:13][CH2:12][CH2:11][CH2:10][C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)(=[O:20])(=[O:19])[NH2:21]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 178496789HCID 178496789, compound

Product 1

HCID 178512633HCID 178512633, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.3 g of methyl 5-(2-guanidinothiazol-4-yl)pentanoimidate and 1.1 g of sulfamide were dissolved in 4.3 g of methanol, and the solution was allowed to stand overnight at room temperature. The solvent was distilled away under reduced pressure and the residue was purified by a silica gel column chromatography using a mixture of acetone and methanol as the developing solvent. The obtained crystals were dissolved in 0.4 ml of acetic acid, 4 ml of ehtanol and 8 ml of water, and the solution was treated with activated charcoal. To the filtrate was added 6.6 ml of N--NaOH, and the precipitated crystals were filtered off to provide 0.70 g of N-sulfamoyl-5-(2-guanidinothiazol-4-yl)pentanoamidine having a melting point of 156°-157° C.

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. customthe residue was purified by a silica gel column chromatography
  3. additiona mixture of acetone and methanol as the developing solvent
  4. dissolutionThe obtained crystals were dissolved in 0.4 ml of acetic acid
  5. addition4 ml of ehtanol and 8 ml of water, and the solution was treated with activated charcoal
  6. additionTo the filtrate was added 6.6 ml of N
  7. filtrationNaOH, and the precipitated crystals were filtered off

Sources & evidence

ORD record
ord-a9b427a2f591481ead2502950f0b7773
Source dataset
uspto-grants-1981_08
Patent number
US04283408

Reaction notes

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