Potassium cyanate → 2-(Diaminomethyleneamino)-4-(2-ureidomethylthiazol-4-yl)thiazole

HRID 2379841Notes

Reaction equation

HRID 2379841 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)[N:7]=1.[O-:17][C:18]#[N:19].[K+]>O>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[N:7]=[C:3]([CH2:2][NH:1][C:18]([NH2:19])=[O:17])[S:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 189538084-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 189537912-(Diaminomethyleneamino)-4-(2-ureidomethylthiazol-4-yl)thiazoleYield 29.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole (1.0 g) and potassium cyanate (0.5 g) in water (50 ml) was stirred for 3.5 hours at room temperature. The resulting precipitate was collected by filtration. The precipitate was suspended in water (30 ml) and then a saturated aqueous potassium carbonate solution (20 ml) was added. The mixture was stirred for 1 hour at room temperature. The resulting precipitate was collected by filtration. Recrystallization from a mixture of methanol and water afforded 2-(diaminomethyleneamino)-4-(2-ureidomethylthiazol-4-yl)thiazole (0.35 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additiona saturated aqueous potassium carbonate solution (20 ml) was added
  3. filtrationThe resulting precipitate was collected by filtration
  4. customRecrystallization
  5. additionfrom a mixture of methanol and water

Sources & evidence

ORD record
ord-5992a17c3b444dd585617984e13c4602
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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