Methanol → HCID 131719932, compound

HRID 962874Notes

Reaction equation

HRID 962874 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-thio-carbamoylbenzoyl) 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-9094993cfb8440c896e9b7656bdc4c47
Source dataset
uspto-grants-1998_06
Patent number
US05760057

Reaction notes

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