Sodium Cyanide → HCID 69892648, compound

HRID 411638Notes

Reaction equation

HRID 411638 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[S:13]([CH2:23][N+:24]#[C-:25])([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[C-]#N.[Na+]>>[C:19]1([CH3:20])[CH:18]=[CH:17][C:16]([S:13]([C@@H:23]2[C@@H:6]([C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=3)[O:7][CH:25]=[N:24]2)(=[O:14])=[O:15])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 8929Sodium CyanideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 69892648HCID 69892648, compound

Procedure

In a manner analogous to Preparation 1, 3-(trifluoromethyl)benzaldehyde (0.16 g, 1.47 mmol), tosylmethylisocyanide (0.27 g, 1.40 mmol) and NaCN (6.9 mg, 0.14 mmol) gave the desired compound as a tan solid. 1H NMR (300 MHz, CDCl3) δ 2.44 (s, 3H), 4.98-5.04 (dd, 1H), 6.08-6.12 (dd, 1H), 7.3-7.42 (d, 2H), 7.50-7.62 (m, 5H), 7.78-7.86 (d, 2H).

Sources & evidence

ORD record
ord-823bdf7ea1fc43b385a1c8089ddbec05
Source dataset
uspto-grants-2003_05
Patent number
US06559172B1

Reaction notes

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