Hydrochloric Acid → HCID 58007609, compound

HRID 1094371Notes

Reaction equation

HRID 1094371 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:4][CH:3]=1.B.O1CCCC1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CC(OC)(C)C.O>[CH3:1][C:2]1[S:6][C:5]([NH:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 17144262HCID 17144262, compound

Product 1

HCID 58007609HCID 58007609, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-(5-methyl-thiazol-2-yl)-2-p-tolyl-acetamide (1.31 g, 5.33 mmol) in THF (11 mL) was added dropwise under a nitrogen atmosphere borane-tetrahydrofuran complex (1 M in THF, 11 mL, 11 mmol). The reaction mixture was stirred for 18 h at 80° C. To the solution was added very carefully a aqueous hydrochloric acid (1 M, 10 mL) and stirred for 30 min at 80° C. After cooling it was diluted with TBME (25 mL), water (20 mL) and basified by addition of Na2CO3. The aqueous layer was extracted with TBME (25 mL) and the organic layers were washed with brine (15 mL). The combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate:methanol=90:10:0 to 40:50:10) afforded the title compound (630 mg, 51%) as a white solid. MS m/e: 233.0 [M+H]+.

Workup

  1. stirringstirred for 30 min at 80° C
  2. temperatureAfter cooling it
  3. extractionThe aqueous layer was extracted with TBME (25 mL)
  4. washthe organic layers were washed with brine (15 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate:methanol=90:10:0 to 40:50:10)

Sources & evidence

ORD record
ord-2fcdd47058f940b1a024939fe961889f
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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