Potassium Iodide → HCID 21260106, compound

HRID 634606Notes

Reaction equation

HRID 634606 reaction equation
[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:28][C:29]([N:31](C)C)=[O:30]>>[CH2:1]([S:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:28][C:29]([NH2:31])=[O:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 179051-OctadecanethiolHCID 31374Dimethylacetamide

Product 1

HCID 21260106HCID 21260106, compound

Conditions

Temperature
100 °C

Procedure

In a 300 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube were charged 13.2 g of octadecanthiol, 14.3 g of 11-bromoundedanamide, 1.7 g of potassium iodide, 20.7 g of potassium carbonate and 100 ml of DMAc, and the mixture was stirred at 100° C. for 5 hours. After cooling the reaction mixture to room temperature, the reaction mixture was poured into ice-water and precipitated crystals were collected by filtration under reduced pressure, and washed with distilled water. The resulting crystals were recrystallized from IPA to obtain 16.4 g of the title compound. Melting point: 108° C.

Workup

  1. customIn a 300 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customprecipitated crystals
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with distilled water
  6. customThe resulting crystals were recrystallized from IPA

Sources & evidence

ORD record
ord-6fbdceb0be204ab08b04eaa61328471a
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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