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

HRID 633476Notes

Reaction equation

HRID 633476 reaction equation
SCC(C(CS)O)O.[S:9]([C:12]1[CH:25]=[CH:24][C:15]2[N:16]=[C:17]([NH:19][C:20](=[O:23])[O:21][CH3:22])[S:18][C:14]=2[CH:13]=1)C#N>O.C(O)C.P([O-])(O)(O)=O.[K+]>[SH:9][C:12]1[CH:25]=[CH:24][C:15]2[N:16]=[C:17]([NH:19][C:20](=[O:23])[O:21][CH3:22])[S:18][C:14]=2[CH:13]=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-1387f4564c384700b5bde8e6e5f60289
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

Loading…