Triethylamine → 2-(Diaminomethyleneamino)-4-[2-(3-methylureido)methylthiazol-4-yl]thiazole

HRID 1491850Notes

Reaction equation

HRID 1491850 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[N:16]=[C:17]([N:20]=[C:21]([NH2:23])[NH2:22])[S:18][CH:19]=2)[N:14]=1.[CH3:24][N:25]=[C:26]=[O:27]>CO>[NH2:22][C:21](=[N:20][C:17]1[S:18][CH:19]=[C:15]([C:13]2[N:14]=[C:10]([CH2:9][NH:8][C:26]([NH:25][CH3:24])=[O:27])[S:11][CH:12]=2)[N:16]=1)[NH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 189538084-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 189538032-(Diaminomethyleneamino)-4-[2-(3-methylureido)methylthiazol-4-yl]thiazoleYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.7 g) was added to a suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole (1.0 g) in methanol (20 ml). To the mixture was added methylisocyanate (0.21 g). The mixture was stirred at room temperature for 1.5 hours. The solvent was removed under the reduced pressure and the residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1). Recrystallization from a mixture of water and methanol afforded 2-(diaminomethyleneamino)-4-[2-(3-methylureido)methylthiazol-4-yl]thiazole (0.5 g).

Workup

  1. customThe solvent was removed under the reduced pressure
  2. customthe residue was chromatographed on a silica gel column
  3. washeluting with a mixture of chloroform and methanol (10:1)
  4. customRecrystallization
  5. additionfrom a mixture of water and methanol

Sources & evidence

ORD record
ord-0cc6546762c44743a21267b4986c6f78
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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