Reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14]C)[CH2:12]C)=[O:7])=[C:4]([O:19]C)[CH:3]=1.NC1C(Cl)=CC(C(NCCN(C)C)=O)=C(OC)C=1>>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:14])[CH3:12])=[O:7])=[C:4]([OH:19])[CH:3]=1Participants
Procedure
The general procedure of Preparation 1A was repeated except that the 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide utilized therein was replaced by 4-amino-5-chloro-N-[2-(dimethylamino)ethyl]-2-methoxybenzamide (prepared according to U.K. Pat. No. 1,793,771). The solvent (DMF) was removed in vacuo, and the residue treated with water and methylene chloride saturated with carbon dioxide, concentrated, and the crude product isolated in 89% yield by extraction with ethanol. A sample was chromatographed on a silica gel column usimg methylene chloride (97), methanol (3), ammonia (0.3) solvent system. The appropriate fractions were combined and concentrated in vacuo. The residue was crystallized from methanol to give the title compound as a colorless solid, mp. 163°-165°.
Workup
- customprepared
- customThe solvent (DMF) was removed in vacuo
- additionthe residue treated with water and methylene chloride saturated with carbon dioxide
- concentrationconcentrated
- customthe crude product isolated in 89% yield by extraction with ethanol
- customA sample was chromatographed on a silica gel column usimg methylene chloride (97), methanol (3), ammonia (0.3) solvent system
- concentrationconcentrated in vacuo
- customThe residue was crystallized from methanol
Sources & evidence
- ORD record
- ord-6127a8d94fc743ae828eae8a2d912673
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04820715
Linked notes
Loading…