Acetone → HCID 23369998, compound

HRID 1900875Notes

Reaction equation

HRID 1900875 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:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([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+:41]>ClCCl.CO>[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:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:15][CH:14]=2)=[O:9])=[CH:6][CH:5]=1)(=[NH:41])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370029HCID 23370029, compound

Product 1

HCID 23369998HCID 23369998, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, t-butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (4.4 g) was reacted with iodomethane (25 ml) and acetone (450 ml) and the resultant product was treated with ammonium acetate (10 g), methanol (400 ml) and dichloromethane (100 ml) at ambient temperature. This yielded a crude yellow solid (1.2 g), which was triturated with methanol, collected, washed with methanol and then stirred with 50% aqueous acetic acid solution (15 ml). Any solid material was filtered and discarded and the filtrate was evaporated and triturated under a mixture of ether and methanol to give the title compound (300 mg) as an off-white solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 1.77 (1.8H, s), 4.62 (2H, s), 6.90 (2H, d), 7.49 (2H, d), 7.92 (2H, d), 8.15 (2H, d), 9.50-10.4 (3H, br), 10.60 (1H s); Mass Spectrum m/Z 413 (M+H)+ ; Elemental Analysis: calculated for C21H24N4O5. 0.6 CH3CO2H. 1.5 H2O: C, 56.0%; H, 6.2%; N, 11.7%; found: C, 56.3%; H, 6.2%; N, 11.1%.

Workup

  1. customThis yielded a crude yellow solid (1.2 g), which
  2. customwas triturated with methanol
  3. customcollected
  4. washwashed with methanol
  5. filtrationAny solid material was filtered
  6. customthe filtrate was evaporated
  7. customtriturated under a mixture of ether and methanol

Sources & evidence

ORD record
ord-f084b03ace3a425fbfdfd1681d4fd042
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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