Methanol → HCID 131719933, compound

HRID 962876Notes

Reaction equation

HRID 962876 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-thio-carbamoylbenzoyl) 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-b42a050bd35d4f4990ba9964c4f46e1d
Source dataset
uspto-grants-1998_06
Patent number
US05760057

Reaction notes

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