Methanol → HCID 131719933, compound

HRID 977029Notes

Reaction equation

HRID 977029 reaction equation
[CH3:1][N:2]([NH:17][C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=S)[NH2:26])=[CH:21][CH:20]=1)[C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].IC.C([O-])(=O)C.[NH4+:35].CO>CC(C)=O.ClCCl>[C:11]([OH:13])(=[O:12])[CH3:10].[CH3:1][N:2]([NH:17][C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:35])[NH2:26])=[CH:21][CH:20]=1)[C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 19610500HCID 19610500, compound

Product 1

HCID 131719933HCID 131719933, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 12, methyl 4-[2-methyl-3-(4-thiocarbamoylbenzoyl)carbazoyl]phenoxyacetate (2.5 g) was reacted with iodomethane (15 ml) in acetone (150 ml) and the resultant product was treated with ammonium acetate (6.5 g), methanol (100 ml) and dichloromethane (100 ml). This yielded a crude yellow solid, which was triturated with methanol, collected and washed with methanol/dichloromethane, rather than crystallised, to give the title compound (1.3 g) as an off-white solid; m.p. 210° C. (decomposes); NMR Spectrum (DMSO-d6) 1.73 (3H, s), 3.20 (3H, s), 3.55 (3H, s), 4.76 (2H, s), 6.90 (2H, d), 7.53 (2H, d), 7.80 (4H, m), 8.50-11.0 (2H, br s); Mass Spectrum m/Z 385 (M+H)+ ; Elemental Analysis: calculated for C19H20N4O5. 1.0 CH3CO2H. 0.8 H2O: C, 55.0%; H, 5.6%; N, 12.2%; found: C, 55.0%; H, 5.4%; N, 11.8%.

Workup

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

Sources & evidence

ORD record
ord-dfd245dfb38f4961af39c335c7c4485e
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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