Sulfuric Acid → HCID 71542042, compound

HRID 1023178Notes

Reaction equation

HRID 1023178 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][NH:13][C:14](=O)[CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][C:14]([CH2:15][O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86680423HCID 86680423, compound

Product 1

HCID 71542042HCID 71542042, compoundYield 31.3%

Procedure

N-(3,4-dichlorophenyl)-2-(2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetyl)hydrazinecarbothioamide (0.15 g, 0.341 mmol) and concentrated sulfuric acid (1 mL) were placed in a reaction beaker and the mixture was subjected to ultrasonic irradiation for 15 min. The reaction contents were poured into ice cold water. The precipitate was filtered and basified with 10% sodium bicarbonate (30 mL). Crude product was crystallized with ethanol/DMSO to afford 6-((5-(3,4-dichlorophenylamino)-1,3,4-thiadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (0.045 g, 31%) as an off white solid. 1H NMR 400 MHZ, DMSO-d6: δ 2.42 (dd, J=7.20, 8.20 Hz, 2H), 2.85 (t, J=7.60 Hz, 2H), 5.37 (s, 2H), 6.79 (d, J=8.80 Hz, 1H), 6.88 (dd, J=2.40, 8.60 Hz, 1H), 6.95 (d, J=2.00 Hz, 1H), 7.48 (dd, J=2.40, 8.80 Hz, 1H), 8.08 (d, J=2.80 Hz, 1H), 9.96 (s, 1H), 10.75 (s, 1H). LCMS: RT 1.97 min, LCMS (ES-API), m/z 423.0 (M+H).

Workup

  1. customthe mixture was subjected to ultrasonic irradiation for 15 min
  2. customThe reaction contents
  3. additionwere poured into ice cold water
  4. filtrationThe precipitate was filtered
  5. customCrude product was crystallized with ethanol/DMSO

Sources & evidence

ORD record
ord-7ca891224552478086741984202eafd7
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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