Methanol → HCID 131719933, compound

HRID 1602726Notes

Reaction equation

HRID 1602726 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-fee597e159ef4430a84033f619ae49a4
Source dataset
uspto-grants-1999_11
Patent number
US05981531

Reaction notes

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