Piperonal → HCID 12116612, compound

HRID 1838652Notes

Reaction equation

[S:1]([CH2:11][N+:12]#[C-:13])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH:14]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]2[O:22][CH2:23][O:24][C:16]=2[CH:15]=1.[C-]#N.[Na+]>>[O:24]1[C:16]2[CH:15]=[CH:14][C:19]([C@@H:20]3[O:21][CH:13]=[N:12][C@@H:11]3[S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])=[CH:18][C:17]=2[O:22][CH2:23]1

Participants

Reactant 3

HCID 8438Piperonal

HCID 8929Sodium Cyanide

HCID 161915Tosylmethyl isocyanide

Product 1

HCID 12116612HCID 12116612, compound

Procedure

In a manner analogous to Preparation 1, tosylmethylisocyanide (0.23 g, 1.20 mmol), piperonal (0.19 g, 1.26 mmol) and NaCN (5.9 mg, 0.12 mmol) gave the desired compound as a tan solid. MS(ES+) m/z 346.5 (M+H+).

Sources & evidence

ORD record: ord-ccee8890dd694671b0dafbf8ebabedf5
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673941B2

Reaction notes

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