Trimethylsilyldiazomethane → HCID 58119307, compound

HRID 2167488Notes

Reaction equation

HRID 2167488 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[CH3:29][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:29])=[O:25])=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 58119322HCID 58119322, compound

Product 1

HCID 58119307HCID 58119307, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3-oxazol-4-yl}benzoic acid from Step A (32 mg, 0.077 mmol) was dissolved in MeOH (0.5 mL) and DCM (0.5 mL). Trimethylsilyl diazomethane (2.0 M in ether) was slowly added at 0° C. until a yellow color persisted. The volatiles were evaporated to give methyl 4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3-oxazol-4-yl}benzoate which was used without further purification. LCMS: m/z 421.1 (M+H)+.

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-171f81d71c9749e68752f34af229432f
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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