Sodium Cyanide → HCID 69567970, compound

HRID 411639Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[S:14]([CH2:24][N+:25]#[C-:26])([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[C-]#N.[Na+]>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[C@H:4]1[O:5][CH:26]=[N:25][C@@H:24]1[S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

Reactant 3

HCID 8929Sodium Cyanide

HCID 161915Tosylmethyl isocyanide

HCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 69567970HCID 69567970, compound

Procedure

In a manner analogous to Preparation 1, 2-fluoro-5-(trifluoromethyl)benzaldehyde (0.26 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 2.48 (s, 3H), 5.10-5.14 (dd, 1H), 6.12-6.16 (dd, 1H), 7.16-7.20 d, 2H), 7.40-7.44 (dd, 2H), 7.52-7.56 (d, 1H), 7.66-7.70 (d, 1H), 7.88-7.92 (dd, 2H).

Sources & evidence

ORD record: ord-c50a515061d04554816568779e4490a2
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559172B1

Reaction notes

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