Trimethylsilyldiazomethane → HCID 786481, compound

HRID 1924444Notes

Reaction equation

HRID 1924444 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:4].[CH3:17][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[F:1][C:2]([F:15])([F:16])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:17])=[O:11])=[CH:13][CH:14]=1)=[O:4]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2890744-[(trifluoroacetyl)amino]benzoic acid

Product 1

HCID 786481HCID 786481, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

step b To a solution of 120 (4.29 g, 18.40 mmol) in MeOH (50 mL) and toluene (75 mL) was added dropwise trimethylsilyldiazomethane (15.64 mL, 31.3 mmol) until the yellow color persisted. The resulting solution was stirred for 30 min then the reaction was quenched with several drops of HOAc until the yellow color disappeared. The solvents were evaporated to afford methyl 4-(2,2,2-trifluoro-acetylamino)-benzoate (122) which was used in the next reaction without further purification.

Workup

  1. customthe reaction was quenched with several drops of HOAc until the yellow color
  2. customThe solvents were evaporated

Sources & evidence

ORD record
ord-1817abca70254d44802b1080503ff17b
Source dataset
uspto-grants-2012_05
Patent number
US08178547B2

Reaction notes

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