Ethanol → HCID 54112251, compound

HRID 1395038Notes

Reaction equation

HRID 1395038 reaction equation
[C:1]([CH:4]=[CH:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[C:16](=[O:17])[C:15]([Cl:18])=[N:14][S:13][N:12]=2)=[CH:8][CH:7]=1)([OH:3])=[O:2].[CH2:21](N(CC)CC)[CH3:22].C(O)C>S(Cl)(Cl)=O.C(Cl)Cl.O>[Cl:18][C:15]1[C:16](=[O:17])[C:11]([O:10][C:9]2[CH:19]=[CH:20][C:6]([CH:5]=[CH:4][C:1]([O:3][CH2:21][CH3:22])=[O:2])=[CH:7][CH:8]=2)=[N:12][S:13][N:14]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 53668196HCID 53668196, compound

Product 1

HCID 54112251HCID 54112251, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A stirred solution of 15.5 grams (0.05 mole) of 3-[4-(2-carboxyethenyl)phenoxy]-5-chloro-4H-1,2,6-thiadiazin-4-one in 150 ml of thionyl chloride was heated under reflux for 16 hours, then allowed to cool to ambient temperature. The excess thionyl chloride was removed under reduced pressure to give a residual solid. The solid was dissolved in 300 ml of methylene chloride. To the resulting solution was carefully added 6.1 grams (0.06 mole) of triethylamine; then, dropwise, 4.6 grams (0.1 mole) of absolute ethanol. The reaction mixture was stirred at ambient temperature for 2.5 hours, then diluted with 150 ml of water. The organic layer was separated and washed with 200 ml of water, then 150 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a solid residue. The solid was recrystallized twice with ethanol to give 8.7 grams (51%) of 3 -chloro-5-[4-(2-ethoxycarbonylethenyl)phenoxy]-4H-1,2,6-thiadiazin-4-one; mp 126°-127.5° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe excess thionyl chloride was removed under reduced pressure
  3. customto give a residual solid
  4. customThe organic layer was separated
  5. washwashed with 200 ml of water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure to a solid residue
  9. customThe solid was recrystallized twice with ethanol

Sources & evidence

ORD record
ord-797491445df64383b7cb20491f6558af
Source dataset
uspto-grants-1980_05
Patent number
US04201780

Reaction notes

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