Hydrochloric Acid → HCID 53326303, compound

HRID 1966890Notes

Reaction equation

HRID 1966890 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][C:14]([CH3:17])=[N:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:18](Cl)(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl>N1C=CC=CC=1>[CH3:17][C:14]1[S:13][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:18](=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:16][N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5328SulfamethizoleHCID 66982Decanoyl chloride

Product 1

HCID 53326303HCID 53326303, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

Compound 105 (250 mg, 0.93 mmol) was suspended in pyridine (0.5 mL). Decanoyl chloride (141 mg, 0.74 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 (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 (297 mg, 0.70 mmol, 95%) as a solid, mp 141-142° C.; 1H NMR (500 MHz, DMSO) δ 0.82 (3, t, J=7.0 Hz), 1.10-1.30 (12, m), 1.54-1.63 (2, m), 2.32 (2, t, J=7.0 Hz), 2.45 (3, s), 8.25 (2, d, J=8.0 Hz), 8.28 (2, d, J=8.0 Hz), 10.25 (1, s), 13.87 (1, s); 13C NMR (125 MHz, DMSO) δ 13.9, 16.0, 22.1, 24.9, 28.5, 28.6, 28.8, 28.9, 31.2, 36.4, 118.5, 126.8, 135.5, 142.7, 154.1, 167.6, 171.7; MS (LCQ, ESI+) Calculated for C19H29N4O3S2 425.2, found 425.1 (M+H)+; HRMS (FAB+, m/z) Calculated for C19H29N4O3S2 425.1681, found 425.1678 (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-1f24bab1051a428c9cec1042bdb8f6d3
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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