Trichloroacetyl isocyanate → HCID 514447, compound

HRID 1862474Notes

Reaction equation

HRID 1862474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18][OH:19])[C:11]=2[CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:31]([N:33]=C=O)=[O:32]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:16])[CH3:17])[N:13]=[C:12]([CH2:18][O:19][C:31](=[O:32])[NH2:33])[C:11]=2[CH2:20][O:21][CH2:22][C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 10203491HCID 10203491, compound

Product 1

HCID 514447HCID 514447, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 120 mg of 5-(3,5-Dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methoxymethyl]-1H-pyrazole-3-methanol in 1 ml of dichloromethane at 0° C. was added 11 mg of trichloroacetyl isocyanate. The mixture was stirred for 2 h at 0° C. then the solvent was removed. The residue was dissolved in 2 ml of methanol and 1 ml of water, 100 mg of potassium carbonate added, and the mixture stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and water. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography using methanol/dichloromethane for the elution to give 12 mg of carbamic acid [5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methoxymethyl]-1H-pyrazol-3-yl]methyl ester as a white solid. Mass spectrum (ES) m/z 481 [M]+. 1H NMR (DMSO-d6) 1.25 (d, 6H), 4.50 (s, 2H), 4.52 (s, 2H), 4.80 (m, 1H), 5.05 (s, 2H), 6.55 (br s, 1H), 6.75 (br s, 1H), 7.08 (m, 2H), 7.16 (d, 2H) 7.45 (m, 1H), 8.43 (d, 2H).

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in 2 ml of methanol
  3. addition1 ml of water, 100 mg of potassium carbonate added
  4. stirringthe mixture stirred at room temperature for 1 h
  5. customThe mixture was partitioned between ethyl acetate and water
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography
  10. washfor the elution

Sources & evidence

ORD record
ord-fdf2c0f8008345b78439f09718fa173a
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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