N-(2,4-Dimethylphenyl)acetamide → 3,4-Dihydro-2,6,8-trimethylquinazolin-4-one
Reaction equation
C1C=CC2N=C[NH:9][C:7](=[O:8])C=2C=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([CH3:22])=O)=[C:15]([CH3:23])[CH:14]=1>>[CH3:22][C:20]1[NH:9][C:7](=[O:8])[C:17]2[C:16](=[C:15]([CH3:23])[CH:14]=[C:13]([CH3:12])[CH:18]=2)[N:19]=1Participants
Procedure
The quinazolinone used as starting material was obtained using the first part of the process described in Example 1 concerning the preparation of starting materials except that 2,4-dimethylacetanilide was used in place of 3,4-dimethylacetanilide. Only one isomer, 3,4-dihydro-2,6,8-trimethylquinazolin-4-one, was obtained. Sodium hydride (2.39 g) was added to a stirred suspension of the product thus obtained (9.3 g) in dimethylformamide (100 ml) and the mixture was stirred at laboratory temperature for 1 hour. A solution of chloromethyl pivalate (8.23 ml) in dimethylformamide (20 ml) was added and the mixture was stirred at laboratory temperature for 18 hours, then poured onto a mixture of ice water (350 ml). The precipitate was filtered off, dried and purified by chromatography on a silica gel column using methylene chloride as eluent. There was thus obtained 3,4-dihydro-2,6,8-trimethyl-3-pivaloyloxymethylquinazolin-4-one (8.7 g).
Workup
- customwas obtained
Sources & evidence
- ORD record
- ord-b84fbdcc11a44f3ca2b41189fe19f086
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04981856
Reaction notes
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