Potassium Bromide → HCID 66613626, compound

HRID 1404708Notes

Reaction equation

HRID 1404708 reaction equation
[O:1]=[C:2]([CH3:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:9][NH:10][C:11]1[S:12][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:14][N:15]=1.[K+].[Br-]>ClC(Cl)C>[CH3:9][N:10]([C:11]1[S:12][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:14][N:15]=1)[C:5](=[O:6])[CH2:4][CH2:3][C:2](=[O:1])[CH3:8]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 6488196N-methyl-5-(pyridin-3-yl)-1,3,4-thiadiazol-2-amineHCID 123004064-Oxopentanoyl chloride

Product 1

HCID 66613626HCID 66613626, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

4-oxopentanoyl chloride (0.378 g, 2.8 mmol) was added to a suspension of N-methyl-5-(3-pyridyl)-1,3,4-thiadiazol-2-amine (0.3 g, 1.6 mmol) and 4-N,N-dimethylaminopyridine (0.229 g, 1.9 mmol) in dichloroethane (5 mL), stirred under nitrogen at room temperature for 30 minutes, refluxed for 14 hours, cooled, diluted with dichloroethane (50 mL) and washed with saturated aqueous sodium bicarbonate (70 mL). The aqueous layer was extracted with dichloroethane (30 mL) and the combined organic layers were dried over MgSO4, adsorbed on silica, applied to a Michel-Miller column and eluted with 9:1 ethyl acetate/hexane. The major fraction was collected and recrystallized from ethyl acetate/hexane to afford yellow needles. Yield 0.21 g (46%): mp 146-147° C.; IR (KBr, thin film) 1701, 1659 cm−1; 1HNMR (400 MHz, CDCl3) δ 9.13 (d, J=1.8 Hz, 1H), 8.69 (dd, J=4.8, 1.5 Hz, 1H), 8.28 (dt, J=6.2, 1.9 Hz, 1H), 7.42 (dd, J=8.0, 5.1 Hz, 1H), 3.90 (s, 3H), 2.96 (br, 4H), 2.29 (s, 3H); ESIMS m/z 291 ([M+H]+).

Workup

  1. temperaturerefluxed for 14 hours
  2. temperaturecooled
  3. washwashed with saturated aqueous sodium bicarbonate (70 mL)
  4. extractionThe aqueous layer was extracted with dichloroethane (30 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. washeluted with 9:1 ethyl acetate/hexane
  7. customThe major fraction was collected
  8. customrecrystallized from ethyl acetate/hexane
  9. customto afford yellow needles

Sources & evidence

ORD record
ord-27d3ef8f2c2c4ec0a83e0546bc80e6be
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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