Acetone → HCID 131719659, compound

HRID 1900905Notes

Reaction equation

HRID 1900905 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11](=[O:27])[NH:12][C:13]2[CH:26]=[CH:25][C:16]([O:17][CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:15][CH:14]=2)=[O:9])=[CH:6][CH:5]=1)(=S)[NH2:2].IC.CC(C)=O.C([O-])(=O)C.[NH4+:40]>ClCCl.CO>[C:19]([OH:21])(=[O:20])[CH3:18].[C:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11](=[O:27])[NH:12][C:13]2[CH:26]=[CH:25][C:16]([O:17][CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:15][CH:14]=2)=[O:9])=[CH:6][CH:5]=1)(=[NH:40])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370031HCID 23370031, compound

Product 1

HCID 131719659HCID 131719659, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, isopropyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (10.88 g) was reacted with iodomethane (60 ml) and acetone (600 ml) at ambient temperature and the resultant product was treated with ammonium acetate (12 g), methanol (220 ml) and dichloromethane (220 ml). This yielded, after filtering the reaction mixture whilst hot and evaporating the filtrate to near dryness, a pale yellow solid, which was slurried in dichloromethane and stirred at ambient temperature overnight, filtered and the solid dissolved in hot methanol. After cooling, the precipitated solid was collected and washed with dichloromethane to give the title compound (2.4 g) as a pale yellow solid: m.p. >300° C. (decomposes); NMR Spectrum (DMSO-d6) 1.29 (6H, d), 4.77 (2H, s), 5.06 (1H, m), 6.97 (2H, d), 7.54 (2H, d), 7.97 (2H, d), 8.20 (2H, d), 10.75 (1H, br s); Mass Spectrum m/Z 399 (M+H)+ ; Elemental Analysis: calculated for C20H22N4O5. 1.0 CH3CO2H. 0.5 H2O: C, 56.5%; H, 5.8%; N, 12.0%; found: C, 56.7%; H, 5.9%; N, 11.9%.

Workup

  1. filtrationThis yielded, after filtering the reaction mixture whilst hot and
  2. customevaporating the filtrate
  3. filtrationfiltered
  4. dissolutionthe solid dissolved in hot methanol
  5. temperatureAfter cooling
  6. customthe precipitated solid was collected
  7. washwashed with dichloromethane

Sources & evidence

ORD record
ord-c1177839064b4c43b8feaa4972f46a36
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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