Hydrochloric Acid → HCID 12112401, compound

HRID 1792782Notes

Reaction equation

HRID 1792782 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:16]([CH3:18])[CH3:17])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=1.O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:16]([CH3:18])[CH3:17])=[C:11]([CH2:13][CH2:14][O:15][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 12112400HCID 12112400, compound

Product 1

HCID 12112401HCID 12112401, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a mixture of methylene chloride (1 mL) and pyridine (2 mL) was dissolved 2-[2-(2-chlorophenyl)-5-isopropyloxazol-4-yl]ethanol (159 mg, 0.598 mmol). Under cooling with water, to the solution was added p-toluenesulfonyl chloride (125 mg, 0.658 mmol). The mixture was stirred for 5 hours. The reaction mixture was poured into 1N HCl and extracted with chloroform. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate=2/1), to obtain the desired compound (123 mg, 49%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-d60196164a8444fbb56e9ca8a2f88c55
Source dataset
uspto-grants-2006_07
Patent number
US07078422B2

Reaction notes

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