Succinic Acid → HCID 20388952, compound

HRID 426937Notes

Reaction equation

HRID 426937 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][N:6]=1.[OH-].[Na+].C(O)(=O)CCC(O)=O>Cl.C(OCC)(=O)C.CO>[CH3:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][CH2:9][NH2:10])=[CH:5][N:6]=1

Participants

7

Reactant 3

HCID 1110Succinic AcidHCID 14798Sodium HydroxideHCID 20388950HCID 20388950, compound

Product 1

HCID 20388952HCID 20388952, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 19 g of the product of Step F in 100 ml of concentrated hydrochloric acid was refluxed for 16 hours and was then iced. Concentrated sodium hydroxide solution was slowly added thereto to adjust the pH to 12-13 and the mixture was extracted with ethyl acetate. The extracts were dried and evaporated to dryness under reduced pressure to obtain 11 g of raw product which was dissolved in ethyl acetate. A solution of 10% succinic acid in methanol was added thereto until the pH was 7 and the mixture was iced and vacuum filtered. The recovered product was dried and was crystallized from isopropanol to obtain 11.8 g of the hemisuccinate of 2-methyl-5-thiazole-propanamine melting at 170° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. customto obtain 11 g of raw product which
  5. filtrationvacuum filtered
  6. customThe recovered product was dried
  7. customwas crystallized from isopropanol

Sources & evidence

ORD record
ord-b6723eb7240b414e90be21a65236ac66
Source dataset
uspto-grants-1979_10
Patent number
US04172137

Reaction notes

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