Acetone → HCID 131719649, compound

HRID 1900879Notes

Reaction equation

HRID 1900879 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]([NH:12][C:13](=[O:30])[NH:14][C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=2)=[O:11])=[CH:6][CH:5]=1)(=S)[NH2:2].IC.CC(C)=O.C([O-])(=O)C.[NH4+:41]>ClCCl.CO>[C:21]([OH:23])(=[O:22])[CH3:20].[C:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]([NH:12][C:13](=[O:30])[NH:14][C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=2)=[O:11])=[CH:6][CH:5]=1)(=[NH:41])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370042HCID 23370042, compound

Product 1

HCID 131719649HCID 131719649, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, t-butyl 4-[3-(6-thiocarbamoylpyrid-3-ylcarbonyl)ureido]phenoxyacetate (2.73 g) was reacted with iodomethane (13 ml) and acetone (200 ml) and the resultant product was treated with ammonium acetate (6 g), methanol (30 ml) and dichloromethane (30 ml) at ambient temperature. This yielded a crude solid which was collected and washed with methanol and acetone to give the title compound (1.68 g) as an orange solid: m.p. 290°-300° C. (decomposes); NMR Spectrum (DMSO-d6) 1.43 (9H, s), 1.82 (3H, s), 4.62 (2H, s), 6.90 (2H, d), 7.49 (2H, d), 8.29 (1H, d), 8.52 (1H, dd), 9.18 (1H, d) 10.61 (1H, s); Mass Spectrum m/Z 414 (M+H)+ ; Elemental Analysis: calculated for C20H23N5O5. 1.0 CH3CO2H. 0.5 H2O: C, 54.8%; H, 5.85%; N, 14.5%; found: C, 54.6%; H, 6.0%; N, 14.5%

Workup

  1. customThis yielded a crude solid which
  2. customwas collected
  3. washwashed with methanol and acetone

Sources & evidence

ORD record
ord-c5875644858e4741b13f454250fd5242
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

Loading…