Acetone → HCID 131719654, compound

HRID 1900896Notes

Reaction equation

HRID 1900896 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([C:8]([NH:10][C:11](=[O:28])[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][C:14]=2[CH3:27])=[O:9])=[CH:6][CH:5]=1)(=S)[NH2:2].IC.CC(C)=O.C([O-])(=O)C.[NH4+:41]>ClCCl.CO>[C:19]([OH:21])(=[O:20])[CH3:18].[C:1]([C:4]1[CH:30]=[CH:29][C:7]([C:8]([NH:10][C:11](=[O:28])[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][C:14]=2[CH3:27])=[O:9])=[CH:6][CH:5]=1)(=[NH:41])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370011HCID 23370011, compound

Product 1

HCID 131719654HCID 131719654, compoundYield 117.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, isopropyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate (12.23 g) was reacted with iodomethane (100 ml) and acetone (750 ml) at ambient temperature and the resultant product was treated with ammonium acetate (15.4 g), methanol (350 ml) and dichloromethane (300 ml) at ambient temperature for 3 days and then at reflux for 5 hours. The mixture was filtered whilst hot, diluted with ether to turbidity and stored overnight at 10° C. to give a solid which was collected, washed with methanol/dichloromethane/ether, 1:1:2 (100 ml) and with ether and dried to give the title compound (7.88 g) as a pale yellow solid: NMR Spectrum (DMSO-d6) 1.23 (6H, d), 2.28 (3H, s), 4.71 (2H, s), 5.01 (1H, m), 6.77 (1H, dd), 6.86 (1H, d), 7.78 (1H, d), 7.91 (2H, d), 8.15 (2H, d), 10.55 (1H, br s); Elemental Analysis: calculated for C21H24N4O5. 1.0 CH3CO2H. 0.21H2O: C, 58.0%; H, 6.01%; N, 11.8%; found: C, 57.4%; H, 6.1%; N, 11.5%.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe mixture was filtered whilst hot,
  3. additiondiluted with ether to turbidity
  4. customto give a solid which
  5. customwas collected
  6. washwashed with methanol/dichloromethane/ether, 1:1:2 (100 ml) and with ether
  7. customdried

Sources & evidence

ORD record
ord-355b1cf7ee034eeeb2f46fc2266441d3
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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