Sodium Cyanide → HCID 69556169, compound

HRID 411629Notes

Reaction equation

[S:1]([CH2:11][N+:12]#[C-:13])([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:14]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15].[C-:27]#N.[Na+]>>[C:14]([O:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:23]2[O:24][CH:13]=[N:12][C@@H:11]2[S:1]([C:4]2[C:5]([CH3:27])=[CH:6][CH:7]=[CH:9][CH:10]=2)(=[O:2])=[O:3])=[CH:25][CH:26]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

Reactant 3

HCID 8929Sodium Cyanide

HCID 93774p-tert-Butoxybenzaldehyde

HCID 161915Tosylmethyl isocyanide

Product 1

HCID 69556169HCID 69556169, compound

Procedure

In a manner analogous to Preparation 1, tosylmethylisocyanide (0.23 g, 1.20 mmol), 4-(tert-butoxy)benzaldehyde (0.23 g, 1.26 mmol) and NaCN (5.9 mg, 0.12 mmol) gave the desired compound as a tan solid. MS(ES+) m/z 374.4 (M+H+).

Sources & evidence

ORD record: ord-9efe1407c4de42b89826b4edffb55a2b
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559172B1

Reaction notes

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