Trimethylsilyldiazomethane → HCID 67256899, compound

HRID 2427207Notes

Reaction equation

HRID 2427207 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-3b861a8a3f784e8b9e42f3c17ad1a732
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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