Ammonium Chloride → HCID 54011574, compound

HRID 1464303Notes

Reaction equation

HRID 1464303 reaction equation
[Cl-:1].[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC1([CH:33]([C:39]([CH:41](N2C=NC=N2)[C:42]2(Cl)[CH2:44]C2)=O)[N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)CC1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:41]1([C:39](=[CH:5][C:4]2[CH:25]=[CH:26][CH:27]=[CH:28][C:3]=2[Cl:2])[CH2:33][N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)[CH2:42][CH2:44]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2734112(2-Chlorobenzyl)triphenylphosphonium ChlorideHCID 19087882HCID 19087882, compound

Product 1

HCID 54011574HCID 54011574, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

36.6 g (326 mmol) of potassium tert.-butylate are added at 0° C. with stirring, to a solution of 115 g (271 mmol) of 2-chlorobenzyl-triphenylphosphonium chloride in 600 ml of tetrahydrofuran. After the addition has ended, stirring is continued for one hour at 40° C. A solution of 50.4 g (271 mmol) of 1-chlorocyclopropyl-(1,2,4-triazol-1-yl)-methyl ketone in 300 ml of tetrahydrofuran is subsequently added dropwise at 30° C. with stirring. The reaction mixture is stirred for 16 hours at room temperature and then poured into saturated, aqueous ammonium chloride solution. The phases are separated, the aqueous phase is extracted several times using ethyl acetate, and the combined organic phases are dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. The residue which remains is chromatographed on silica gel using a mixture of cyclchexane:ethyl acetate=2:1 as eluent. In this manner, 61.5 g (77% of theory) of 2-(1-chlorocyclopropyl)-1-(1,2,4 -triazol-1-yl)-3-(2-chlorophenyl)-2-propene (E/Z isomer mixture) are obtained in the form of a solid of melting point 82°-85° C.

Workup

  1. additionAfter the addition
  2. stirringwith stirring
  3. stirringThe reaction mixture is stirred for 16 hours at room temperature
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted several times
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue which remains is chromatographed on silica gel using
  9. additiona mixture of cyclchexane

Sources & evidence

ORD record
ord-f444db654e2440f2b1b30f58e7768681
Source dataset
uspto-grants-1994_04
Patent number
US05304568

Reaction notes

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