Water → HCID 21930368, compound

HRID 1243764Notes

Reaction equation

HRID 1243764 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]N(C)C)[C:12]=2[S:21][CH2:22][CH3:23])[CH:3]=1.[Cl:24]C(OCC)=O.O.C(OCC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][Cl:24])[C:12]=2[S:21][CH2:22][CH3:23])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10928Ethyl chloroformateHCID 10154693HCID 10154693, compound

Product 1

HCID 21930368HCID 21930368, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 4-chloro-2-(3-dimethylaminomethyl-2-ethylsulfanyl-phenoxy)-benzonitrile (570 mg, 1.64 mmol) was dissolved in anhydrous toluene (10 mL). The solution was cooled to 0° C. and ethyl chloroformate (480 μL, 5 mmol) was slowly added. The reaction mixture was stirred for 17 h, allowing it to reach room temperature. Water (5 mL) and diethyl ether (5 mL) were added and the organic layer was separated and dried with MgSO4. After filtration, the solvent was removed in vacuo to yield crude material (340 mg) that was then dissolved in ethyl acetate and absorbed in vacuo onto silica gel (1.5 g). This material was chromatographed on an ISCO CombiFlash Chromatography System to yield 4-chloro-2-(3-chloromethyl-2-ethylsulfanyl-phenoxy)-benzonitrile as a clear oil (240 mg, 43%).

Workup

  1. customto reach room temperature
  2. customthe organic layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationAfter filtration
  5. customthe solvent was removed in vacuo
  6. customto yield crude material (340 mg) that
  7. customabsorbed in vacuo onto silica gel (1.5 g)
  8. customThis material was chromatographed on an ISCO CombiFlash Chromatography System

Sources & evidence

ORD record
ord-007fa1c919174498a826ed90dbdf2dec
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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