Hydrochloric Acid → HCID 21279521, compound

HRID 2291215Notes

Reaction equation

HRID 2291215 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[C:12]([SH:14])[NH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:16]([CH3:20])[C:17]([OH:19])=[O:18].Cl.CCOCC>O.[OH-].[Na+]>[CH2:1]([S:8][C:9]1[N:13]=[C:12]([S:14][CH:16]([CH3:20])[C:17]([OH:19])=[O:18])[NH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 117292-Bromopropionic acidHCID 178527897HCID 178527897, compound

Product 1

HCID 21279521HCID 21279521, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

3-Benzylthio-5-mercapto-1,2,4-triazole (56 g) was added with stirring and cooling to a solution of sodium hydroxide (10.1 g) in water (150 ml). A cold solution of 2-bromopropionic acid (38.4 g) in aqueous sodium hydroxide (10 g in 50 ml water) was added dropwise with stirring. The mixture was stirred for a further 6 hours at room temperature and allowed to stand overnight. After acidification with concentrated hydrochloric acid (30 ml), the precipitated white sticky solid was taken into ether. The ether solution was washed with water, dried, and the volume reduced to about 200 ml. The product crystallised, and was isolated by filtration to give 36.1 g of desired product, mp 123°-124° C. Successive reductions of the mother liquors gave further product, giving a total yield of 60 g.

Workup

  1. stirringwith stirring
  2. stirringThe mixture was stirred for a further 6 hours at room temperature
  3. washThe ether solution was washed with water
  4. customdried
  5. customThe product crystallised
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-9138cb93716445bab6801c0d1b721afc
Source dataset
uspto-grants-1989_01
Patent number
US04795483

Reaction notes

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