Guanidine Hydrochloride → HCID 178431914, compound

HRID 1903579Notes

Reaction equation

HRID 1903579 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[Cl:15][C:16]1[S:17][CH:18]=[C:19]([CH3:24])[C:20]=1[N:21]=[C:22]=[O:23]>C1COCC1>[ClH:15].[C:3]([NH:5][C:22]([NH:21][C:20]1[C:19]([CH3:24])=[CH:18][S:17][C:16]=1[Cl:15])=[O:23])(=[NH:2])[NH2:4]

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 13560098HCID 13560098, compound

Product 1

HCID 178431914HCID 178431914, compoundYield 131.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of guanidine hydrochloride (14.33 g), and 50% aqueous NaOH (10.00 g) in THF (250 ml) is stirred at room temperature overnight. THF (250 ml), and anhydrous Na2SO4 (7.5 g) are added to the mixture and stirring continued for 1 hour. A solution of 2-chloro-3-isocyanato-4-methylthiophene (8.68 g) in THF (500 ml) is added dropwise to the stirred mixture. After the addition is complete, stirring is continued for 30 minutes. The solvent is decanted, leaving a THF insoluble material. The solvent is evaporated under reduced pressure. The evaporated residue is suspended in 500 ml of 2% aqueous HCl and added to the THF insoluble material. This mixture is stirred vigorously with 250 ml of Et2O for 30 minutes. Insoluble material is separated by decantation. The aqueous layer is separated, washed with Et2O and alkalinized with NaHCO3, forming a precipitate. The precipitate is washed with H2O and air dried to afford 8.85 g of a tan crystalline solid. The tan solid is dissolved in 5% aqueous HCl (175 ml), filtered through Celite, and the filtrate cooled rapidly to room temperature. After standing overnight in the cold, the precipitate is collected, washed with a portion of the mother liquor, dried in vacuo, and stirred in 100 ml of CH2Cl2, and air dried in vacuo (50° C.) overnight to yield 7.20 g of the amidinourea hydrochloride as a tan powder, m.p. 173°-174.5° C. w/dec.

Workup

  1. stirringstirring
  2. waitcontinued for 1 hour
  3. additionAfter the addition
  4. stirringstirring
  5. waitis continued for 30 minutes
  6. customThe solvent is decanted
  7. customleaving a THF insoluble material
  8. customThe solvent is evaporated under reduced pressure
  9. additionadded to the THF insoluble material
  10. stirringThis mixture is stirred vigorously with 250 ml of Et2O for 30 minutes
  11. customInsoluble material is separated by decantation
  12. customThe aqueous layer is separated
  13. washwashed with Et2O
  14. customforming a precipitate
  15. washThe precipitate is washed with H2O and air
  16. customdried

Sources & evidence

ORD record
ord-a36fc0f6e40f4388abe01a5b7237a613
Source dataset
uspto-grants-1984_03
Patent number
US04436911

Reaction notes

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