Potassium Carbonate → HCID 20290364, compound

HRID 1413705Notes

Reaction equation

HRID 1413705 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([OH:13])=[O:12])[NH:2]1.[OH-].[Na+].BrCCC(Cl)=[O:20].[S:22]1[CH:26]=[CH:25]C=[C:23]1[CH2:27][C:28]([O-:30])=O.[K+].S1C=CC=C1CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:26]([S:22][CH2:23][CH2:27][C:28]([N:2]1[CH:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:30])(=[O:20])[CH3:25]

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 159702-Thiopheneacetic acidHCID 84944Propanoyl chloride, 3-bromo-HCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 20290364HCID 20290364, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5.0 g., 0.028 M) and sodium hydroxide (2.26 g., 0.056 M) in water (100 ml.) at 10° C. is slowly added 3-bromopropionyl chloride (2.84 ml., 0.028 M). This mixture is stirred at 25° C. overnight. Potassium thiolacetate, prepared by mixing thiolacetic acid (3.00 ml., 0.042 M) and potassium carbonate (3.90 g., 0.028 M) in water (30 ml.), is added to the reaction mixture which is stirred at 25° C. overnight to yield the title compound as an alkali metal salt. Acidification with dilute hydrochloric acid affords the free carboxylic acid.

Workup

  1. customat 10° C.
  2. additionis added to the reaction mixture which
  3. stirringis stirred at 25° C. overnight

Sources & evidence

ORD record
ord-094b24797b8c4ed5acab8167ff82caa2
Source dataset
uspto-grants-1981_02
Patent number
US04251444

Reaction notes

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