Tosylmethyl isocyanide → HCID 71001888, compound

HRID 2274457Notes

Reaction equation

HRID 2274457 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:15]=O)[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.CC1C=CC(S([CH2:27][N+:28]#[C-])(=O)=O)=CC=1.CC([O-])(C)C.[K+]>COCCOC>[CH3:1][C:2]1[N:3]=[C:4]([CH2:15][C:27]#[N:28])[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1

Participants

5

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 86714576HCID 86714576, compound

Product 1

HCID 71001888HCID 71001888, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Same procedure as that described in example 1, stage 1.4, starting from 8.7 g (32.7 mmol) of 4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde, 6.7 g (34.3 mmol) of TOSMIC and 7.3 g (65 mmol) of potassium tert-butylate in solution in anhydrous DME (54 ml). 6.6 g of compound is obtained in the form of a yellow oil as 70/30 mixture of regioisomers tau and Pi.

Sources & evidence

ORD record
ord-4d3060c79fbf4c1c8ea55ca1f1661540
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

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