Acetonitrile → HCID 178503631, compound

HRID 1990114Notes

Reaction equation

HRID 1990114 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]#[N:17])=[C:14]([S:18][CH3:19])[S:13][C:12]=2[C:20]([NH2:22])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC#N.[N-:26]=[N+:27]=[N-:28].[Na+].[Si](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]#[N:17])=[C:14]([S:18][CH3:19])[S:13][C:12]=2[C:20]2[NH:22][N:28]=[N:27][N:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 68524423HCID 68524423, compound

Product 1

HCID 178503631HCID 178503631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid amide (0.142 mmol) and 1.5 ml CH3CN with NaN3 (0.43 mmol) and SiCl4 (0.142 mmol) in CH2Cl2 and reflux the mixture for 16 hrs. MS shows desired product and starting material. Conc. to dryness and purification by radial chromatography (Si) on a 1000 micron plate eluting with 5% MeOH/0.5% AcOH/CH2Cl2. Concentrate desired fractions to provide the desired title compound: 1H NMR (400 MHz, CDCl3) δ 7.40 (q, 4H, J=22 Hz), 2.73 (s, 3H), and 1.35 (s, 9H), MS found (M+1) 356.2.

Sources & evidence

ORD record
ord-621c37349a744250833d33de31a36a1c
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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