Trimethylsilyldiazomethane → HCID 67256899, compound

HRID 1824382Notes

Reaction equation

HRID 1824382 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][C:15]=2[N:16]=1.[CH3:24][Si](C=[N+]=[N-])(C)C>CO.C1COCC1.CCCCCC>[CH3:24][O:22][C:21]([C:18]1[CH:19]=[CH:20][C:14]2[S:13][C:12]([S:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[Cl:1])=[N:16][C:15]=2[CH:17]=1)=[O:23]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22148775HCID 22148775, compound

Product 1

HCID 67256899HCID 67256899, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a 0.25M solution of 2-(2-chloro-4-nitro-phenylsulfanyl)-benzothiazol-5-carboxylic acid (253), (1.38 g, 3.8 mmol) in 10% MeOH in THF was added a 2M solution of (trimethylsilyl)diazomethane in hexane, obtained from Aldrich, (2.1 mL, 4.18 mmol) and the resulting solution was allowed to stir for 18 hours. The crude reaction mixture was concentrated under vacuum to yield 1.4 g (100%) of ester 254 which was taken on without further purification.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-03b391e8b570414a810a123d477f12c6
Source dataset
uspto-grants-2006_05
Patent number
US07041691B1

Reaction notes

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