Hydrochloric Acid → HCID 68984012, compound

HRID 1815505Notes

Reaction equation

HRID 1815505 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:21][C:22]([OH:24])=[O:23].N1CCCCC1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:21][C:22]([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 11088283HCID 11088283, compound

Product 1

HCID 68984012HCID 68984012, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,3-dichloro-4-(2-methoxyphenylthio)-benzaldehyde (2.03 g), 1.44 g malonic acid, 5 mL pyridine, and 0.100 g piperidine was heated to 115 degrees for 1.5 hours. The mixture was cooled, and ice and HCl were added. The resulting solid was: filtered, washed with water and dissolved in tetrahydrofuran. This solution was dried over sodium sulfate, the solvent removed and ether added to give 1.733 g of product, m.p. 187-188 C.

Workup

  1. temperaturewas heated to 115 degrees for 1.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washwashed with water
  5. dissolutiondissolved in tetrahydrofuran
  6. dry with materialThis solution was dried over sodium sulfate
  7. customthe solvent removed
  8. additionether added

Sources & evidence

ORD record
ord-e7c4077b4bc948b6840d079a7747a91a
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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