3-Mercaptopropionic Acid → CGP 20376

HRID 1905947Notes

Reaction equation

HRID 1905947 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N:14]=[C:15]=[S:16])[C:11]([O:17][CH3:18])=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[SH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]>CN(C)C=O>[C:22]([CH2:21][CH2:20][S:19][C:15](=[S:16])[NH:14][C:12]1[C:11]([O:17][CH3:18])=[CH:10][C:8]2[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6][C:7]=2[CH:13]=1)([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 65143-Mercaptopropionic AcidHCID 173314Cgp 20308

Product 1

HCID 3035447CGP 20376

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.8 g (0.10 mole) of 2-tert.-butyl-6-isothiocyano-5-methoxy-benzthiazole are dissolved in 150 ml of dimethylformamide and 14 g (0.13 mole) of 3-mercaptopropionic acid are added. The solution is stirred at room temperature under nitrogen for 2 hours, then poured onto 2 kg of ice and stirred until the product has become solid. It is filtered off, washed with water and heated in 700 ml of toluene, decanted from water, dried over sodium sulphate, clarified with active carbon and filtered. The filtrate is diluted at 30°-40° with approximately 700 ml of petroleum ether and cooled slowly to 5°, filtered off and subsequently washed with petroleum ether. N-[2-tert.-butyl-5-methoxy-benzthiazol-6-yl]-dithiocarbamic acid S-(2-carboxyethyl)-ester having a melting point of 154°-156° is obtained: ##STR14##

Workup

  1. stirringstirred until the product
  2. filtrationIt is filtered off
  3. washwashed with water
  4. temperatureheated in 700 ml of toluene
  5. customdecanted from water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. additionThe filtrate is diluted at 30°-40° with approximately 700 ml of petroleum ether
  9. temperaturecooled slowly to 5°
  10. filtrationfiltered off
  11. washsubsequently washed with petroleum ether

Sources & evidence

ORD record
ord-c1f4a6bf8019499e8dcefaa0b916fac5
Source dataset
uspto-grants-1987_03
Patent number
US04649149

Reaction notes

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