Hydrochloric Acid → HCID 17733931, compound
Reaction equation
CC1(C)OC(=O)CC(=O)O1.C1(N=C=O)C=CC=CC=1.Cl.[NH:21]([C:28]([OH:39])=[C:29]1[C:34](=[O:35])OC(C)(C)OC1=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:40][O:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[NH2:44]>CN(C=O)C>[CH3:40][O:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[NH:44][C:34](=[O:35])[CH2:29][C:28]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:39]Participants
Procedure
Meldrum's Acid (5.0 g, 34.7 mmol) was added to a flask along with DMF (40 ml) and TEA (10 ml, 70 mmol). The mixture was allowed to stir for 5 minutes and phenyl isocyanate (4.13 g, 34.7 mmol) was added. The contents of the flask were allowed to stir for 30 minutes. The mixture was poured into a flask containing HCl (200 ml) and ice. The solid was filtered and dried in vacuo overnight to afford product as a white solid. 5-[anilino(hydroxy)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (100 mg, 0.380 mmol) was added to a microwave vial along with o-methoxyaniline (51 mg, 0.418 mmol) and 1 ml of DMF. The vial was capped and microwaved at 165° C. for 10 minutes. The contents of the vial were concentrated and purified by trituration with DCM to afford the product, N-(2-methoxyphenyl)-N′-phenylmalonamide as an off-white solid. ESIMS calcd 285.2 (M++H), found 285.3 (M++H)
Workup
- stirringto stir for 30 minutes
- additionThe mixture was poured into a flask
- filtrationThe solid was filtered
- customdried in vacuo overnight
- customto afford product as a white solid
- customThe vial was capped
- custommicrowaved at 165° C. for 10 minutes
- concentrationThe contents of the vial were concentrated
- custompurified by trituration with DCM
Sources & evidence
- ORD record
- ord-0e1a0f51a5ca460b8ecdfb710eb06298
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158825B2
Reaction notes
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