Acetic Acid → HCID 21498921, compound

HRID 1730081Notes

Reaction equation

HRID 1730081 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=O)[CH2:7][CH:8]2[C:13](=O)[CH2:12][CH2:11][S:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18][N:19]([CH2:21][CH2:22][NH2:23])[CH3:20].C(O)(=O)C.Cl>O>[CH3:18][N:19]([CH3:20])[CH2:21][CH2:22][N:23]1[C:6]([C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:9][S:10][CH2:11][CH2:12][C:13]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 66053N,N-DimethylethylenediamineHCID 21498910HCID 21498910, compound

Product 1

HCID 21498921HCID 21498921, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.0 g (0.019 mole) of 3-(4-chlorophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, 7.14 g of dimethylaminoethylamine and 15 ml. of acetic acid is heated under reflux under nitrogen for 24 hours, diluted with water, acidified with hydrochloric acid, extracted with ether, neutralized with sodium hydroxide, and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated. The residue is recrystallized from ethanol to give off-white crystals of 1-(2-dimethylaminoethyl)-2(4-chlorophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole, m.p. 91.5° to 92.5°C.

Workup

  1. temperatureunder reflux under nitrogen for 24 hours
  2. extractionextracted with ether
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-43639ee90d004574a4f4bfeb4fd4422d
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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