Hydrochloric Acid → HCID 20350647, compound

HRID 1449236Notes

Reaction equation

HRID 1449236 reaction equation
[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]=[C:24]([S:27](C)=O)SC)[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(Cl)Cl.[OH2:34].[CH3:35][O:36][CH2:37][CH2:38][O:39]C>>[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:37][C:38]([OH:39])=[O:34])[C:9]1[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:36][CH3:35])=[S:27])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 54175266HCID 54175266, compound

Product 2

HCID 13023173HCID 13023173, compoundYield 14%HCID 20350647HCID 20350647, compoundYield 81%

Conditions

Temperature
80 °C

Procedure

In 26 ml of 1,2-dimethoxyethane, 1.2 g (0.0026 mole) of 1-[N-benzyl-o-(2,6-dichloroanilino)phenyl]-2-methylsulfinyl-2-methylthioethylene was dissolved and then, 13 ml of conc. HCl was added and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled and 80 ml of methylene chloride and 10 ml of water were added to extract the reaction product and the separated water phase was further mixed with 70 ml of methylene chloride to extract the reaction product. Both of methylene chloride phases were combined, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was separated by a column chromatography (silica gel: Wako gel Q-23 manufactured by Wako Junyaku and developing solvent:n-hexane:acetone=2:1) to obtain 0.14 g (yield: 14%) of N-benzyl-o-(2,6-dichloroanilino)phenyl acetic acid and 0.88 g (yield: 81%) of methyl N-benzyl-o-(2,6-dichloroanilino)phenylthioacetate.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionto extract the reaction product
  3. additionthe separated water phase was further mixed with 70 ml of methylene chloride
  4. extractionto extract the reaction product
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by a column chromatography (silica gel: Wako gel Q-23 manufactured by Wako Junyaku and developing solvent:n-hexane:acetone=2:1)

Sources & evidence

ORD record
ord-ddffbd3595b24f63825b6be4d2dae32e
Source dataset
uspto-grants-1980_02
Patent number
US04189595

Reaction notes

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