Acetic Acid → HCID 21498929, compound

HRID 1730084Notes

Reaction equation

HRID 1730084 reaction equation
[CH2:1]([CH:10]1[C:15](=O)[CH2:14][CH2:13][S:12](=[O:18])(=[O:17])[CH2:11]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[CH3:19][N:20]([CH2:22][CH2:23][CH2:24][NH2:25])[CH3:21].C(O)(=O)C.Cl>O>[CH3:19][N:20]([CH3:21])[CH2:22][CH2:23][CH2:24][N:25]1[C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:1][C:10]2[CH2:11][S:12](=[O:18])(=[O:17])[CH2:13][CH2:14][C:15]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21498934HCID 21498934, compound

Product 1

HCID 21498929HCID 21498929, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.0 g (0.0075 mole) of 3-phenacyl-2,3,5,6-tetrahydrothiopyran-4-one-1,1-dioxide, 0.85 g of dimethylaminopropylamine and 30 ml. of acetic acid is heated under reflux for 5 hours. The reaction solution is cooled, diluted with water, adjusted to a pH of 1 with hydrochloric acid, and then washed with ether. The solution is made basic with sodium bicarbonate and extracted with ether. The ether extract is dried and concentrated to a solid. The solid is recrystallized from 2-propanol to give off-white needles of 1-(3-dimethylaminopropyl)-2-phenyl-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole-5,5-dioxide, m.p. 123° to 125°C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureThe reaction solution is cooled
  3. washwashed with ether
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. customis dried
  7. concentrationconcentrated to a solid
  8. customThe solid is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-03551a2d9dd241efb14467b5a54bdcc5
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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