2-Propanone, 1-(acetyloxy)-3-chloro- → HCID 25261017, compound

HRID 1966208Notes

Reaction equation

HRID 1966208 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:19][C:20](=O)[CH2:21][O:22][C:23](=[O:25])[CH3:24]>CN(C=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[S:16][CH:19]=[C:20]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[N:17]=2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 86644601HCID 86644601, compound

Product 1

HCID 25261017HCID 25261017, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

(5-Phenoxy-pyridine-2-yl)-thiourea (0.86 mmol) is dissolved in DMF (1 ml) and acetic acid 3-chloro-2-oxo-propyl ester (1.1 eq.) in 1 ml DMF is added and stirred 2 h at 70° C. After cooling to RT the precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. “A9” is obtained after column chromatography (heptan/ethyl acetate) as colourless powder in a yield of 69%; mp. 158.5-160.5° C.; HPLC (method C): 1.89 min; LC-MS (method A): 1.938 min, 342.15 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.375 (s, 1H), 8.105 (d, 1H, J=2.8 Hz), 7.519 (dd, 1H, J=8.9 Hz, J=2.8 Hz), 7.389-7.347 (m, 2H), 7.120-7.088 (m, 2H), 6.995-6.978 (m, 2H), 6.918 (s, 1H), 5.007 (s, 2H), 2.064 (s, 3H).

Workup

  1. temperatureAfter cooling to RT the precipitate
  2. filtrationis filtered
  3. washwashed with water
  4. dry with materialdried 16 h in vacuo at 40° C. “A9”
  5. customis obtained after column chromatography (heptan/ethyl acetate) as colourless powder in a yield of 69%
  6. custom1.89 min
  7. custom1.938 min, 342.15 (M+H+)

Sources & evidence

ORD record
ord-8080673b29994b5ba1f7082575005514
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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