Ammonium Chloride → HCID 22647545, compound

HRID 1767922Notes

Reaction equation

HRID 1767922 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH:7]=[O:8].[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[CH2:25][CH2:26][Mg]Br.[NH4+].[Cl-]>O1CCCC1>[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[CH2:25][CH2:26][CH:7]([C:6]1[S:5][C:4]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)=[N:3][C:2]=1[CH3:1])[OH:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 178419673HCID 178419673, compound

Product 1

HCID 22647545HCID 22647545, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde (200 mg, 0.74 mmol) in tetrahydrofuran (2 ml) was added slowly a 0.5 M solution of (1,3-dioxan-2-ylethyl)magnesiumbromide in tetrahydrofuran (2.06 ml, 1.03 mmol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred 1 h at ambient temperature, saturated aqueous NH4Cl solution was added (15 ml) and the mixture was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give 280 mg (0.72 mmol, 98%) of the title compound as colorless oil which was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted two times with ethyl acetate
  2. washThe combined organic layers were washed two times with brine/ice water 1/1
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-597d9b2f572e44e78538a3d9f20f0119
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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