Dimethylformamide → 7-Fluoro-3-methylquinazoline-2,4(1H,3H)-dione

HRID 1644423Notes

Reaction equation

HRID 1644423 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:5]=1C(NC)=O.ClC(OC1C=CC=CC=1)=[O:17].[CH3:25][N:26]([CH3:29])[CH:27]=[O:28]>>[F:14][C:12]1[CH:13]=[C:4]2[C:5]([C:27](=[O:28])[N:26]([CH3:29])[C:25](=[O:17])[NH:3]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 15891Phenyl chloroformate2×HCID 24758Sodium hydrideHCID 569516612-amino-4-fluoro-N-methylbenzamide2×

Product 1

HCID 667752467-Fluoro-3-methylquinazoline-2,4(1H,3H)-dioneYield 51%

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (60% in mineral oil, 368 mg, 9.2 mmol) in dimethylformamide (12 mL) was cooled to 0° C. and treated with 2-amino-4-fluoro-N-methylbenzamide [Intermediate 137] (0.67 g, 4.0 mmol). Phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added over 40 minutes. After 1 hour a further portion of phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added. The reaction was allowed to warm to room temperature and stir for two hours. The reaction was slowly added to 200 mL of ice. The solid was filtered, washed with methanol to obtain the product (395 mg, 51%).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-5c893c729abf46009d6dbc18632f6616
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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