Ammonium Chloride → HCID 12815959, compound

HRID 1388541Notes

Reaction equation

HRID 1388541 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[F:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[S:18][C:19]1[CH:26]=[CH:25][C:24]([S:27][C:28]([F:31])([F:30])[F:29])=[CH:23][C:20]=1[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([CH:21]([OH:22])[C:20]2[CH:23]=[C:24]([S:27][C:28]([F:31])([F:29])[F:30])[CH:25]=[CH:26][C:19]=2[S:18][C:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=2[F:10])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 12815954HCID 12815954, compound

Product 1

HCID 12815959HCID 12815959, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of a Grignard reagent is prepared by a reaction of 12.0 g of 4-chloro-1-methylpiperidine with 2.4 g of magnesium in 70 ml of tetrahydrofuran and is treated dropwise for 10 minutes with a solution of 21.2 g of 2-(2,5-difluorophenylthio)-5(trifluoromethylthio)benzaldehyde in 40 ml of tetrahydrofuran. The mixture is refluxed for 5 hours and, after cooling, decomposed with a 20% ammonium chloride solution and extracted with benzene. The extract is washed with water, dried with potassium carbonate and evaporated. There are obtained 26.9 g of crude oily α-(1-methyl-4-piperidyl)-2-(2,5-difluorophenylthio)-5-(trifluoromethylthio)benzyl alcohol which is used in this state for further reaction.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. extractionextracted with benzene
  3. washThe extract is washed with water
  4. dry with materialdried with potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-79a89058f24d4064a58ceeb67c78c1e2
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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