Methyl iodide → HCID 19610506, compound

HRID 1602722Notes

Reaction equation

HRID 1602722 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([C:8]([NH:10][NH:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[O:13])=[O:9])=[CH:6][CH:5]=1)(=[S:3])[NH2:2].I[CH3:29]>CC(C)=O>[CH3:29][S:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][NH:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[O:13])=[O:9])=[CH:26][CH:27]=1)=[NH:2]

Participants

4

Reactant 2

HCID 6328Methyl iodide3×HCID 19610525HCID 19610525, compound

Product 1

HCID 19610506HCID 19610506, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
42.5 °C

Procedure

Methyl 4-[3-(4-thiocarbamoylbenzoyl)carbazoyl]phenoxyacetate (10.5 g) was suspended in acetone (1 L) and iodomethane (100 ml) was added. The reaction mixture was heated to 40-45° C. with stirring for 4 hours and then cooled to ambient temperature before a further aliquot of iodomethane (20 ml) was added. The reaction mixture was stirred at ambient temperature overnight. A further aliquot of iodomethane (20 ml) was added and the reaction mixture was heated again to 40-45° C. with stirring for 3 hours. Removal of the solvents in vacuo yielded methyl 4-[3-[4-(methylthio)carbonimidoylbenzoyl]carbazoyl]phenoxyacetate as an orange-brown solid which was not purified further. A portion of the residue (10 g) was suspended in a mixture of methanol (300 ml) and dichloromethane (300 ml), and covered with a blanket of argon before a solution of dry ammonium acetate (27 g) in methanol (100 ml) was added. The reaction mixture was stirred under argon for 2-3 days. Removal of the solvents in vacuo yielded a solid residue which was crystallised, with filtration, from boiling methanol to give the title compound (8.57 g) as a pale yellow solid; m.p. 208-210° C. (decomposes); NMR Spectrum (DMSO-d6) 1.76 (3H, s), 3.72 (3H, s), 4.91 (2H, s), 7.06 (2H, d), 8.05 (2H, d), 7.90 (4H, m); Mass Spectrum m/Z 371 (M+H)+ ; Elemental Analysis: calculated for C18H18N4O5. 1.0 CH3CO2H. 1.0 CH3OH. 1.0 H2O: C, 52.5%; H, 5.87%; N, 11.7%; found: C, 52.1%; H, 6.0%; N, 11.7%.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at ambient temperature overnight
  3. temperaturethe reaction mixture was heated again to 40-45° C.
  4. stirringwith stirring for 3 hours
  5. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-e8f2191b33734624b83ca6b2e52c8982
Source dataset
uspto-grants-1999_11
Patent number
US05981531

Reaction notes

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