Dimethyl Sulfide → Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

HRID 583693Notes

Reaction equation

HRID 583693 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][C:8]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=O.CSC>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][CH2:8][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 18928580Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

Product 1

HCID 18928557Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Amide 24-3 (1.0 g, 3.4 mmol) was dissolved in 7 mL toluene at 0°, and BH3.DMS (341 μL, 3.6 mmol) was added. After 15 min, the reaction was heated to reflux for 16 h, cooled to 0°, and quenched with 10% Na2CO3. The mixture was extracted with EtOAc, the organic phase was washed with water and brine, dried (MgSO4), concentrated, and purified by flash chromatography (silica, 70% EtOAc/hexane) providing 24-4 as a white solid. Rf 0.64 (silica, EtOAc).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 h
  3. temperaturecooled to 0°
  4. customquenched with 10% Na2CO3
  5. extractionThe mixture was extracted with EtOAc
  6. washthe organic phase was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (silica, 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-23d2597344324be4a5ccd85f6bff66d1
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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