Trimethylsilyldiazomethane → HCID 57855940, compound

HRID 2039616Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:16])=[C:4]([CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[NH:11][CH3:12])[C:5]([OH:7])=[O:6].[CH3:17][Si](C=[N+]=[N-])(C)C>C1COCC1.CO>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]([NH:11][CH3:12])=[C:2]([Cl:1])[C:3]=1[F:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5.30 g (21.32 mmol) of 3-chloro-2-fluoro-4-methylamino-5-nitro-benzoic acid in 53 mL of THF and 13.75 ml of MeOH is cooled to a temperature of 0° C. Then, 13.86 ml (27.72 mmol) of trimethylsilyl-diazomethane (2 M in diethylether) were added portion wise at a temperature of 0° C. The mixture is stirred 30 min at a temperature of 0° C. and 30 min at ambient temperature. The reaction mixture is evaporated with acetic acid in the trap. The yellow residue is titurated in diethyl ether and after decantation, 4.3 g (16.37 mmol, 77%) of a yellow solid is isolated. The Et2O phase is evaporated and 1.5 g of impure product is recovered. The crude product is used directly in the next step without purification. 1H-NMR (CDCl3, 300 MHz): ? ppm=3.30 (d, 3H), 3.95 (s, 3H), 7.80 (s br, 1H), 8.70 (d, 1H).

Workup

customThe reaction mixture is evaporated with acetic acid in the trap

Sources & evidence

ORD record: ord-df8386d686bb4e3ab1d2ac905f9ed9ec
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580785B2

Reaction notes

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