3-Mercaptopropionic Acid → 2-(3,4,5-Trimethoxyphenyl)-1,3-perhydrothiazine-4-one

HRID 647066Notes

Reaction equation

HRID 647066 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[SH:15][CH2:16][CH2:17][C:18]([OH:20])=O.C(=O)([O-])[O-].[NH4+:25].[NH4+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:5]([CH:6]2[S:15][CH2:16][CH2:17][C:18](=[O:20])[NH:25]2)[CH:4]=1

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 517111Ammonium Carbonate

Product 1

HCID 30680352-(3,4,5-Trimethoxyphenyl)-1,3-perhydrothiazine-4-oneYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 19.6 g of 3,4,5-trimethoxybenzaldehyde, 10.6 g of 3-mercaptopropionic acid and 6 g of ammonium carbonate in 250 ml of benzene was refluxed for 5 hours at 80° C. in a flask provided with a Dean-Stark apparatus and the thus distilled water was removed. The crystals which separated out from the reaction mixture after reaction was over and on cooling the reaction mixture, were collected by filtration and recrystallized from benzene to give 21.8 g of colourless aciculates melting at 181° to 182° C. in a yield of 77%.

Workup

  1. customprovided with a Dean-Stark apparatus
  2. customthe thus distilled water was removed
  3. customThe crystals which separated out from the reaction mixture
  4. customafter reaction
  5. temperatureon cooling the reaction mixture
  6. filtrationwere collected by filtration
  7. customrecrystallized from benzene
  8. customto give 21.8 g of colourless aciculates melting at 181° to 182° C. in a yield of 77%

Sources & evidence

ORD record
ord-2c20b0dc8b254777981bdfdf79831d80
Source dataset
uspto-grants-1983_10
Patent number
US04407799

Reaction notes

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