Isopropyl iodide → HCID 69127194, compound

HRID 1960226Notes

Reaction equation

HRID 1960226 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].[CH2:7]([Li])[CH2:8][CH2:9]C.CCCCCC.[C:18]1([N:24]=[C:25]=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.IC(C)C>C1COCC1>[C:18]1([N:24]=[C:25]([S:26][CH:8]([CH3:9])[CH3:7])[CH2:2][CH2:1][Si:3]([CH3:6])([CH3:5])[CH3:4])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 7673Phenyl IsothiocyanateHCID 66111TrimethylsilylacetyleneHCID 178418244HCID 178418244, compound

Product 1

HCID 69127194HCID 69127194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Ethynyltrimethylsilane (0.93 g) was dissolved to dry THF (30 ml), n-butyl lithium/hexane solution (1.6 mol/l; 5.6 ml) was added dropwise thereto at −78° C., then it was warmed to 0° C. The reaction mixture was cooled to −78° C., THF (5 ml) solution of phenyl isothiocyanate (1.24 g) was added dropwise to the reaction mixture. Then it was gradually warmed to 0° C. After that, THF (5 ml) solution of 2-iodopropane (1.52 g) was added dropwise thereto under ice-cooling, then stirred for 14 hours at room temperature. The reaction solution was concentrated. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=15/1) to obtain isopropyl N-phenyl-3-(trimethylsilyl)thiopropioimidate (1.7 g).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. temperatureThen it was gradually warmed to 0° C
  4. temperatureunder ice-cooling
  5. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-43d8ed3587b241d0ad6dcce44a608758
Source dataset
uspto-grants-2013_04
Patent number
US08410316B2

Reaction notes

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