Methanol → 5-(2-Amino-1,3-benzothiazol-6-yl)imidazolidine-2,4-dione

HRID 892333Notes

Reaction equation

HRID 892333 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:13](=[O:16])([O-])[O-].[NH4+:17].[NH4+:18].[C-]#N.[Na+].[CH3:22][OH:23]>O>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]3[NH:18][C:22](=[O:23])[NH:17][C:13]3=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 138215412-Aminobenzo[d]thiazole-6-carbaldehyde

Product 1

HCID 138215425-(2-Amino-1,3-benzothiazol-6-yl)imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

22.5 g (0.126 mol) of 1b, dissolved in 400 ml of methanol, are added dropwise to a solution of 50.9 g (0.531 mol) of ammonium carbonate and 9.6 g (0.196 mol) of sodium cyanide in 400 ml of water, and the mixture is stirred at 60° C. for 20 hours. After the methanol has been removed by distillation in vacuo, the remaining solution is acidified, at 0° C., to pH 2 with 2N HCl, then the pH is returned to 4 with 2N sodium hydroxide solution, and the precipitated product is filtered off with suction.

Workup

  1. customAfter the methanol has been removed by distillation in vacuo
  2. customis acidified, at 0° C., to pH 2 with 2N HCl
  3. filtrationthe precipitated product is filtered off with suction

Sources & evidence

ORD record
ord-3da1ff122f6c4e92a7c09a8bc6f98508
Source dataset
uspto-grants-1992_06
Patent number
USRE033948

Reaction notes

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