Sodium Iodide → HCID 69414185, compound

HRID 851890Notes

Reaction equation

HRID 851890 reaction equation
[O:1]=[S:2]1(=[O:23])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:20][CH2:21][CH2:22][CH:4]2[NH:3]1.C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-].Br[CH2:33][CH2:34][O:35][CH2:36][CH2:37]Br>CC#N>[N:19]1([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:9]2[CH:10]=[CH:11][C:6]3[N:5]4[CH2:20][CH2:21][CH2:22][CH:4]4[NH:3][S:2](=[O:1])(=[O:23])[C:7]=3[CH:8]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 10215256HCID 10215256, compound

Product 1

HCID 69414185HCID 69414185, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 300 mg (0.90 mmol) of {3-[(5,5-dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo-[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}amine, 192 mg of Na2CO3 (1.81 mmol), 5 mg of NaI, 126 μl of 2-bromoethyl ether (0.905 mmol) in 6 ml of CH3CN is refluxed overnight. The suspension is filtered; the filtrate is evaporated, taken up in CH2Cl2 and washed with saturated NaCl solution. After evaporation in vacuo, the expected product is purified by chromatography on silica (CH2Cl2/acetone 96/4).

Workup

  1. temperatureis refluxed overnight
  2. filtrationThe suspension is filtered
  3. customthe filtrate is evaporated
  4. washwashed with saturated NaCl solution
  5. customAfter evaporation in vacuo
  6. customthe expected product is purified by chromatography on silica (CH2Cl2/acetone 96/4)

Sources & evidence

ORD record
ord-a8d3d08c25114a4baffd9246c4713034
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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