1,4-Dimercapto-2,3-butanediol → HCID 44604316, compound

HRID 1035745Notes

Reaction equation

HRID 1035745 reaction equation
SCC(C(CS)O)O.[CH3:9][O:10][C:11](=[O:25])[NH:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([S:22]C#N)[CH:19]=[CH:18][C:16]=2[N:17]=1>O.C(O)C.P([O-])(O)(O)=O.[K+]>[CH3:9][O:10][C:11](=[O:25])[NH:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([SH:22])[CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

6

Reactant 2

HCID 190011,4-Dimercapto-2,3-butanediolHCID 86647873HCID 86647873, compound

Product 1

HCID 44604316HCID 44604316, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 516951Monobasic potassium phosphateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

a solution of 5 mg of potassium dihydrogen phosphate in 1.1 cm3 of water at 20° C., followed by 480 mg of DL-dithiothreitol, are added to a white suspension of 280 mg of methyl(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate in 11 cm3 of ethanol at 20° C. The white suspension is stirred for 18 h at reflux. The reaction mixture is cooled to 20° C., then 10 cm3 of water are added and the mixture is stirred for 15 minutes. The precipitate is spin-filter-dried and then washed with large volumes of water. 231 mg of methyl(6-sulphanyl-1,3-benzothiazol-2-yl)carbamate are obtained in the form of a cream powder, the characteristics of which are as follows:

Workup

  1. customat 20° C.
  2. temperatureat reflux
  3. stirringthe mixture is stirred for 15 minutes
  4. customThe precipitate is spin-filter-dried
  5. washwashed with large volumes of water

Sources & evidence

ORD record
ord-49e41f47d7e742b88e346f68d53cbec7
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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