Hydrochloric Acid → HCID 53321030, compound

HRID 1966891Notes

Reaction equation

HRID 1966891 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][C:14]([CH2:17][CH3:18])=[N:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>N1C=CC=CC=1>[CH2:17]([C:14]1[S:13][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:19](=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:16][N:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7181SulfaethidoleHCID 66982Decanoyl chloride

Product 1

HCID 53321030HCID 53321030, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

Compound 109 (250 mg, 0.88 mmol) was suspended in pyridine (1.3 mL). Decanoyl chloride (134 mg, 0.70 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred for 1 h. The reaction mixture was then added to aqueous 3 N HCl solution (4.5 mL) and the mixture extracted with ethyl acetate (3×10 mL). The organic extracts were washed with water (3×20 mL), brine (3×20 mL), dried over anhydrous Na2SO4, and filtered. Evaporation of the solvent left a residue which was crystallized from hexanes and ethyl acetate (1:2) to give the product (372 mg, 0.85 mmol, 97%) as a solid, mp 121-122° C.; 1H NMR (500 MHz, DMSO) δ 0.82 (3, t, J=7.0 Hz), 1.17-1.30 (14, m), 1.57 (2, t, J=7.0 Hz), 2.32 (3, t, J=7.0 Hz), 2.80 (2, q, J=7.0 Hz), 7.72 (2, d, J=8.5 Hz), 7.76 (2, d, J=8.5 Hz), 10.21 (1, s), 13.89 (1, s); 13C NMR (125 MHz, DMSO) δ 12.2, 13.9, 22.1, 23.6, 24.9, 28.6, 28.7, 28.8, 28.9, 31.2, 36.5, 118.5, 126.8, 135.5, 142.7, 159.7, 167.2, 171.8; MS (LCQ, ESI+) Calculated for C20H31N4O3S2 439.2, found 439.1 (M+H)+; HRMS (FAB+, m/z) Calculated for C20H31N4O3S2 439.1838, found 439.1843 (M+H)+.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  2. washThe organic extracts were washed with water (3×20 mL), brine (3×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. waitleft a residue which
  7. customwas crystallized from hexanes and ethyl acetate (1:2)

Sources & evidence

ORD record
ord-817d9b60564843f5bdbed379abb269ca
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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