Anthranilamide → HCID 178482694, compound

HRID 717330Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:11][N:12]([CH3:21])[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[Na].S(=O)(=O)=O>CC(N(C)C)=O.O>[CH3:11][N:12]([CH3:21])[C:13]1[CH:20]=[CH:19][C:16]([C:17]2[N:6]=[C:4]([OH:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:1]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-aminobenzamide (1.36 g, 9.99 mmol, 1.00 equiv) in dimethylacetamide (25 mL), 4-(dimethylamino)benzaldehyde (1.49 g, 9.99 mmol, 1.00 equiv) and sulfonylideneoxidane sodium (1.6 g, 15.53 mmol, 1.50 equiv). The resulting solution was stirred overnight at 150° C. in an oil bath. The reaction mixture was cooled to 25° C. The resulting solution was diluted with 100 mL of water. The solids were collected by filtration. The solid was washed with 2×20 mL of water and 1×20 mL of petroleum ether. This resulted in 2.1 g (79%) of 2-[4-(dimethylamino)phenyl]quinazolin-4-ol as a gray solid. MS (ESI) m/z 266 ([M+H]+).

Workup

customInto a 100-mL 3-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
temperatureThe reaction mixture was cooled to 25° C
filtrationThe solids were collected by filtration
washThe solid was washed with 2×20 mL of water and 1×20 mL of petroleum ether
customThis resulted in 2.1 g (79%) of 2-[4-(dimethylamino)phenyl]quinazolin-4-ol as a gray solid

Sources & evidence

ORD record: ord-b269469599b64e0e88d9b312deaf535b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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