Dimethylformamide → HCID 16103450, compound

HRID 1942855Notes

Reaction equation

HRID 1942855 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].CN(C)C=O.[SH:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1OCCOCCOCCOCCOCCOC1.O>[CH2:8]([C:7]1[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[S:26][C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 66925162HCID 66925162, compound

Product 1

HCID 16103450HCID 16103450, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 962WaterSolvent

Procedure

Compound 59 (35.4 g, 0.13 mol) and K2CO3 (27.6 g, 0.2 mol) were mixed with N,N-dimethylformamide (100 mL). A catalytic amount (˜25 mg) 18-crown-6 was added, and to this mixture, ethyl 2-mercaptoacetate (14.0 mL, 0.13 mol) was added dropwise at 60° C. The mixture was stirred overnight and poured into water (500 mL). The organic component was extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (2×100 mL) and water (100 mL). Organic layer was then dried over MgSO4. After evaporation of the solvent, the crude compound 61 was obtained and purified by column chromatography (SiO2/5% ethyl acetate in hexanes) to yield pure compound 61 (32.1 g, 84.5%). GC/MS: 296 g/mol (M). 1H NMR (CD2Cl2) δ 7.56 (d, 1H), 7.24 (d, 1H), 4.34 (q, 2H), 3.15 (t, 2H), 1.71 (m, 2H), 1.32 (m, 6H), 0.88 (m, 6H). 13C NMR: 163.24, 143.31, 141.85, 141.09, 131.13, 128.44, 120.35, 61.25, 31.99, 29.72 (overlap), 22.98, 14.52, 14.23.

Workup

  1. extractionThe organic component was extracted with ethyl acetate (3×80 mL)
  2. washThe combined organic layers were washed with brine (2×100 mL) and water (100 mL)
  3. dry with materialOrganic layer was then dried over MgSO4
  4. customAfter evaporation of the solvent
  5. customthe crude compound 61 was obtained
  6. custompurified by column chromatography (SiO2/5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9e25e920a04f4ea4bc085fbaf34965d6
Source dataset
uspto-grants-2013_03
Patent number
US08389669B2

Reaction notes

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