2-Methyl-2-thiopseudourea → HCID 178426535, compound

HRID 460747Notes

Reaction equation

HRID 460747 reaction equation
S(O)(O)(=O)=O.[NH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:17])[NH:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].NCCC[C:22]1(C)[NH:26]C(=O)NC1=O.CSC(=N)[NH2:33]>[OH-].[Ba+2].[OH-]>[NH2:33][N:26]=[CH:22][NH:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:17])[NH:14][C:13](=[O:15])[NH:12][C:11]1=[O:16]

Participants

4

Reactant 2

HCID 51422-Methyl-2-thiopseudourea2×HCID 85862277HCID 85862277, compound2×

Product 1

HCID 178426535HCID 178426535, compound

Reagents, catalysts & solvents 1

HCID 6093286Barium hydroxideSolvent3×

Procedure

The compound 5-(3-aminopropyl)-5-methyl-2,4-imidazolidinedione hemisulfate (229 mg, 1 mmol) was dissolved in 0.418 N aqueous barium hydroxide (3.5 ml.) and S-methylisothiourea (153.1 mg, 1.1 mol) was added. The suspension was shaken at room temperature for 6 1/4 hours and 0.418 N aqueous barium hydroxide (1 ml.) was added, followed by another 0.5 ml. of the aforementioned barium hydroxide solution 18 hours later. After 4 hours, S-methylisothiourea (70 mg., 0.5 mmol) was added and shaking of the suspension was continued for 66 hours. At that time only traces of 5-(3-aminopropyl)-5-methyl-2,4-imidazolidinedione hemisulfate could be detected. Barium sulfate was filtered off and washed with water, filtrate and washings were applied to a column containing 5 ml. of sulfonated polystyrene ion exchange resin, the column was washed consecutively with water (50 ml.) 10% by volume aqueous pyridine (25 ml.) and 2.5 M aqueous ammonium hydroxide solution (25 ml). Concentration of the ammoniacal effluent gave a colorless syrup from which crystalline 5-(3-[(aminoiminomethyl) amino]propyl)-5-methyl-2,4-imidazolidinedione was deposited on standing (207 mg., 0.97 mmol, 97%). Recrystallization from water afforded 5-(3-[(amino-iminomethyl)amino]propyl)-5-methyl-2,4-imidazolidienedione as fine needles, m.p. 294°-295° C.

Workup

  1. additionwas added
  2. waitwas continued for 66 hours
  3. filtrationBarium sulfate was filtered off
  4. washwashed with water, filtrate and washings
  5. additioncontaining 5 ml
  6. washof sulfonated polystyrene ion exchange resin, the column was washed consecutively with water (50 ml.) 10% by volume aqueous pyridine (25 ml.) and 2.5 M aqueous ammonium hydroxide solution (25 ml)

Sources & evidence

ORD record
ord-f787f815f8a142fe90cdeda035fe7136
Source dataset
uspto-grants-1977_12
Patent number
US04061542

Reaction notes

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