Methanol → HCID 131719932, compound

HRID 977027Notes

Reaction equation

HRID 977027 reaction equation
[CH3:1][N:2]([C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=S)[NH2:26])=[CH:21][CH:20]=1)[NH:3][C:4]([C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5].[I:29]C.C([O-])(=O)C.[NH4+:35].CO>CC(C)=O.ClCCl>[IH:29].[CH3:1][N:2]([C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:35])[NH2:26])=[CH:21][CH:20]=1)[NH:3][C:4]([C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 19610508HCID 19610508, compound

Product 1

HCID 131719932HCID 131719932, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 12, methyl 4-[3-methyl-3-(4-thiocarbamoylbenzoyl)carbazoyl]phenoxyacetate (2 g) was reacted with iodomethane (15 ml) in acetone (200 ml) and the resultant product was treated with ammonium acetate (5 g), methanol (150 ml) and dichloromethane (150 ml). This yielded a crude yellow solid, which was triturated with methanol/dichloromethane, rather than crystallised, to give the title compound (800 mg) as a pale yellow hydroiodide salt; m.p. 208° C. (decomposes); NMR Spectrum (DMSO-d6) 3.15-3.30 (3H, br), 3.70 (3H, s), 4.86 (2H, s), 6.97 (2H, d), 7.63 (2H, d), 7.67-7.80 (4H, m), 8.70-9.20 (4H, br s); Mass Spectrum m/Z 385 (M+H)+ ; Elemental Analysis: calculated for C19H20N4O5. 1.0 HI. 1.0 H2O: C, 43.0%; H, 4.4%; N, 10.6%; found: C, 43.4%; H, 4.5%; N, 10.1%.

Workup

  1. customThis yielded a crude yellow solid, which
  2. customwas triturated with methanol/dichloromethane
  3. customrather than crystallised

Sources & evidence

ORD record
ord-44edbb36610c4f8abe3f588e017e688c
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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