Sodium Chloride → HCID 22439604, compound

HRID 399380Notes

Reaction equation

HRID 399380 reaction equation
[C:1]([C:5]1[S:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([O:17]C(C)C)[C:14]([Cl:21])=[CH:13][C:12]=2[Cl:22])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[Na+]>C(OCC)C>[C:1]([C:5]1[S:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([OH:17])[C:14]([Cl:21])=[CH:13][C:12]=2[Cl:22])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 18945992HCID 18945992, compound

Product 1

HCID 22439604HCID 22439604, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

11.7 g of 5-t-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-thiadiazol-2(3H)-one (compound Nr. 48; 32.4 mmoles) and 250 ml of methylene chloride are charged into a 500 ml flask in a nitrogen atmosphere. AlCl3 (12.9 g; 96.7 mmoles) is added to this solution in portions and the mixture is maintained under stirring at room temperature for 2 hours. The mixture is then carefully poured into 100 g of ice to which 100 ml of a saturated solution of sodium chloride have been added. 200 ml of ethyl ether are added and, after separation of the phases, the organic phase is washed with a saturated solution of sodium chloride, anhydrified with sodium sulfate and concentrated with a rotavapor. 10 g of the desired product are obtained having m.p. 130°-132° C.

Workup

  1. temperaturethe mixture is maintained
  2. additionhave been added
  3. customafter separation of the phases
  4. washthe organic phase is washed with a saturated solution of sodium chloride
  5. concentrationconcentrated with a rotavapor

Sources & evidence

ORD record
ord-7d0f5aca17d242149502e992fe975a18
Source dataset
uspto-grants-1998_10
Patent number
US05821197

Reaction notes

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