Dimethylformamide → 2-(4-Iodophenyl)-6-(methoxymethyl)-1,3-benzothiazole

HRID 1188747Notes

Reaction equation

HRID 1188747 reaction equation
[H-].[Na+].CN(C=O)C.[I:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22](O)[CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][CH:10]=1.[CH3:25][O:26][CH2:27]Cl>C(N(CC)CC)C>[I:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([CH2:25][O:26][CH3:27])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 67081467HCID 67081467, compound

Product 1

HCID 670817912-(4-Iodophenyl)-6-(methoxymethyl)-1,3-benzothiazoleYield 97.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil; 30 mg, 0.76 mmol) was added to a DMF (2 mL) solution of 5 (225 mg, 0.64 mmol), cooled in an ice bath. After stirring at 0° C. for 1 h, chloromethyl methyl ether (100 μL, 1.33 mmol) and triethylamine (0.2 mL) were added. The reaction mixture was stirred at room temperature overnight and evaporated under reduced pressure. The residue was dissolved in dichloromethane and washed with pH 7 buffer solution (10 mL). The organic phase was dried with anhydrous Na2SO4, filtered, and evaporated to give the crude product. The crude product was purified by flash chromatography on silica gel (CH2Cl2), to give 2-(4-iodophenyl)-6-(methoxymethyl)-1,3-benzothiazole (6) (237 mg, 93.7%) as a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with pH 7 buffer solution (10 mL)
  6. dry with materialThe organic phase was dried with anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product
  10. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-3aeed4fe02a54c629f367c1b9440ad5b
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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