Ammonium Acetate → HCID 131719171, compound

HRID 2211198Notes

Reaction equation

HRID 2211198 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:5].I.CS[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[NH:19][C:20]([C:22]2[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=2)=[O:21])=[CH:13][CH:12]=1)=[NH:10]>CO.ClCCl>[C:1]([OH:4])(=[O:3])[CH3:2].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[NH:19][C:20]([C:22]2[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=2)=[O:21])=[CH:13][CH:12]=1)(=[NH:5])[NH2:10]

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 131719172HCID 131719172, compound

Product 1

HCID 131719171HCID 131719171, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ammonium acetate (1 g) was added to a stirred suspension of methyl 4-[4-(4-methylthiocarbonimidoylphenyl)allophanoyl]phenoxyacetate, hydroiodide salt (340 mg), in methanol (6 ml) and dichloromethane (4 ml). The reaction mixture was stirred at ambient temperature for 3 days and then heated to reflux for 30 hours. The solvents were removed in vacuo and the resultant solid residue was stirred under methanol for 1 hour. The solid was collected and washed with methanol to give the title compound (249 mg) as a white solid; m.p. 225°-229° C. (decomposes); NMR Spectrum (DMSO-d6) 1.75 (3H, s), 3.71 (3H, s), 4.92 (2H, s), 7.07 (2H, d), 7.80 (4H, s), 8.04 (2H, d); Mass Spectrum m/Z 371 (M+H)+ ; Elemental Analysis: calculated for C18H18N4O5. 1.0 CH3CO2H. 0.2 H2O: C, 55.3%; H, 5.2%; N, 12.9%; found: C, 55.4%; H, 5.1%; N, 12.9%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 hours
  3. customThe solvents were removed in vacuo
  4. stirringthe resultant solid residue was stirred under methanol for 1 hour
  5. customThe solid was collected
  6. washwashed with methanol

Sources & evidence

ORD record
ord-0ef9af2eda3043339226e6fae448c5e1
Source dataset
uspto-grants-1995_10
Patent number
US05463011

Reaction notes

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