Dimethylamine → 2-amino-3-fluoro-5-iodo-N,N-dimethyl-benzamide
Reaction equation
[F:1][C:2]1[C:7]2[NH:8]C(=O)[O:10][C:11](=O)[C:6]=2[CH:5]=[C:4]([I:14])[CH:3]=1.[CH3:15][NH:16][CH3:17]>O1CCCC1>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([I:14])=[CH:5][C:6]=1[C:11]([N:16]([CH3:17])[CH3:15])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
550 mg (1.79 mmol) of 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione was combined with 4 mL tetrahydrofuran in a 15 mL-sized sealed tube. To the solution was added 1.79 mL (3.58 mmol) of a 2.0 M dimethylamine solution in tetrahydrofuran. The sealed tube was capped and heated in an oil bath at 60° C. for 48 hours. The solution was concentrated down and then purified by flash chromatography on silica gel. A gradient of ethyl acetate and hexanes was used to afford 368 mg (1.19 mmol, 67% yield) of 2-amino-3-fluoro-5-iodo-N,N-dimethyl-benzamide as a golden oil. 1H NMR (500 MHz, CDCl3) δ 7.29 (dd, 1H), 7.19 (s, 1H), 4.50 (s, br., 2H), 3.03 (s, br., 6H).
Workup
- customsized sealed tube
- customThe sealed tube was capped
- concentrationThe solution was concentrated down
- custompurified by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-d6096eb28e1641fe9b399265c261683a
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709645B2
Reaction notes
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