Potassium Iodide → HCID 89560616, compound

HRID 590400Notes

Reaction equation

HRID 590400 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[S:3]1.Br[CH2:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[OH:17][CH2:16][CH2:15][CH2:14][N:6]1[C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[S:3][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 45077028HCID 45077028, compound

Product 1

HCID 89560616HCID 89560616, compoundYield 128.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde (120 mg, 0.67 mmol), 3-bromopropan-1-ol (85 μL, 0.94 mmol), potassium carbonate (278 mg, 2.01 mmol) and potassium iodide (55 mg, 0.33 mmol) were suspended in acetonitrile (2 mL) and the whole mixture was heated at 65° C. for 48 h. Then, the solids were filtered off and washed with acetonitrile and the resulting filtrate was evaporated to dryness to afford the title compound as a solid (204 mg of 77% purity by HPLC, 99% yield) which was used without further purification.

Workup

  1. filtrationThen, the solids were filtered off
  2. washwashed with acetonitrile
  3. customthe resulting filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2a0f16a4daff42babf5bda2e929bde49
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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