Acetonitrile → HCID 178510279, compound

HRID 2091692Notes

Reaction equation

HRID 2091692 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(#N)C.[Si](Cl)(Cl)(Cl)Cl.C(Cl)Cl.[C:16]([C:18]1[C:19]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[Cl:39])=[C:20]([C:29]([NH2:31])=O)[S:21][C:22]=1[N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)#[N:17]>>[Cl:39][C:33]1[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:32]=1[C:19]1[C:18]([C:16]#[N:17])=[C:22]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:21][C:20]=1[C:29]1[NH:31][N:3]=[N:2][N:1]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 6344Dichloromethane2×HCID 24816Silicon tetrachloride2×HCID 33557Sodium Azide2×HCID 441554464-Cyano-3-(2,4-dichlorophenyl)-5-morpholinothiophene-2-carboxamide

Product 1

HCID 178510279HCID 178510279, compoundYield 54.5%

Procedure

To a mixture of sodium azide (34.01 mg, 0.0005232 mol) in ACN (0.3 mL, 0.005 mol) was added silicon(IV) chloride (0.105 mmol, 0.000105 mol) in DCM (0.1 mL, 0.002 mol) and the mixture was stirred for 30 min. 4-cyano-3-(2,4-dichlorophenyl)-5-morpholinothiophene-2-carboxamide (20.0 mg, 0.0000523 mol) was added to the above mixture, followed by sodium azide (0.0340 g, 0.000523 mol) and silicon(IV) chloride (0.16 mmol, 0.00016 mol) in DCM (0.16 mL, 0.0025 mol) and the mixture was irradiated in microwave at 160° C. for 30 min. The reaction was evaporated and purified by column chromatography to afford 4-(2,4-dichlorophenyl)-2-morpholino-5-(1H-tetrazol-5-yl)thiophene-3-carbonitrile (11.6 mg, 54.4%). LCMS: (FA) ES+ 407.09, ES− 405.20; 1H NMR (300 MHz, d1-chloroform) δ: 7.60 (d, 1H), 7.42 (dd, 1H), 7.30 (d, 1H), 3.90-3.85 (m, 4H), 3.72-3.63 (m, 4H).

Workup

  1. customthe mixture was irradiated in microwave at 160° C. for 30 min
  2. customThe reaction was evaporated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-7734d21ad6944e41b4ef7455967da779
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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