Ethanol → [(1,3,4-Thiadiazol-2,5-diyl)dithio]-bis(2,2'-succinic acid)

HRID 981350

Reaction equation

HRID 981350 reaction equation
[OH-:1].[K+].[CH2:3]([OH:5])[CH3:4].[SH:6][C:7]1[S:8][C:9]([SH:12])=[N:10][N:11]=1.Br[CH:14]([CH2:18][C:19]([OH:21])=[O:20])[C:15]([OH:17])=[O:16]>O>[S:8]1[C:9]([S:12][CH:4]([CH2:14][C:15]([OH:17])=[O:16])[C:3]([OH:1])=[O:5])=[N:10][N:11]=[C:7]1[S:6][CH:14]([CH2:18][C:19]([OH:21])=[O:20])[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 702Ethanol4×HCID 14797Potassium Hydroxide2×HCID 73557Bromosuccinic acidHCID 178418558HCID 178418558, compound

Product 1

HCID 14646898[(1,3,4-Thiadiazol-2,5-diyl)dithio]-bis(2,2'-succinic acid)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 68 g. of a solution of 39.6 g. (0.6 mole) of KOH (85%) in 200 ml. of abs. ethanol is added to a stirred slurry of 15.0 g. (0.1 mole) of 2,5-dimercapto-1,3,4-thiadiazole in 80 ml. of abs. ethanol, at 10°-15° C. The resultant mixture is stirred at 10°-15° C. for half hour thereafter, a clear solution of 39.4 g. (0.2 mole) of bromosuccinic acid in 70 ml. of abs. ethanol is added dropwise over a period of 15 minutes at 10°-15° C. followed by the gradual addition of the remainder of the KOH solution at the same temperature range over a period of 15 minutes. After adding 100 ml. of abs. ethanol, the reaction mixture is stirred in the cooling bath for more than one hour, then overnight in water bath at ambient temperature.

Workup

  1. customat 10°-15° C
  2. additionAfter adding 100 ml
  3. customat ambient temperature

Sources & evidence

ORD record
ord-4d86d0665c834e09a920b9983f2b6ec4
Source dataset
uspto-grants-1991_02
Patent number
US04990652

Linked notes

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