Sodium Cyanide → HCID 69556631, compound

HRID 411625Notes

Reaction equation

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

Participants

Reactant 3

HCID 8929Sodium Cyanide

HCID 227103,4-Dichlorobenzaldehyde

HCID 161915Tosylmethyl isocyanide

Product 1

HCID 69556631HCID 69556631, compound

Procedure

In a manner analogous to Preparation 1, 3,4-dichlorobenzaldehyde (0.56 g, 3.20 mmol), tosylmethylisocyanide (0.75 g, 3.84 mmol) and NaCN (0.02 g, 0.40 mmol) gave the desired compound as a tan solid. 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=8.3 Hz, 2H), 7.50 (d, J=8.3 Hz, 1H), 7.35 (m, 3H), 7.15 (m, 2H), 6.00 (d, J=6.2 Hz. 1H), 4.96 (dd, J=6.2, 1.7 Hz, 1H), 2.47 (s, 3H).

Sources & evidence

ORD record: ord-e3046140c9f04219928696305a2dfa1d
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559172B1

Reaction notes

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