Benzoyl chloride → HCID 11370144, compound

HRID 1592962Notes

Reaction equation

HRID 1592962 reaction equation
[C:1]1([C:7]2([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:16]=[N+:17]([O-])[CH:18]=[CH:19][CH:20]=4)[N:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C1C=CC=CC=1.[CH2:31]([N:33](CC)CC)C.C[Si](C#N)(C)C>CC#N.C(Cl)Cl.CCOC(C)=O.C(Cl)Cl>[C:1]1([C:7]2([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([C:31]#[N:33])=[N:17][CH:16]=4)[N:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 58998533HCID 58998533, compound

Product 1

HCID 11370144HCID 11370144, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]pyridine 1-oxide (2-1, 0.156 g, 01.53 mmol) in anhydrous CH3CN (10.0 mL) was treated with benzoyl chloride (0.073 mL, 0.089 mmol) and triethylamine (0.088 mL, 0.636 mmol) and the mixture was cooled to 0° C. Trimethylsilyl cyanide (0.136 mL, 1.06 mmol) was added and the reaction stirred 48 h at 25° C. The reaction was directly subjected to flash chromatography (SiO2, ISCO 10 g Redi-sep, 1% EtOAc/CH2Cl2) followed by preparative TLC (100% CH2Cl2) and provided 5-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]pyridine-2-carbonitrile (2-2). 1H NMR (300 MHz, CDCl3) δ 9.82 (d, J=1.5 Hz, 1H), 8.31 (dd, J=8.2, 2.2 Hz, 1H), 7.72 (dd, J=8.2, 0.7 Hz, 1H), 7.52 (m, 2H), 7.47 (s, 1H), 7.40 (m, 3H), 1.86 (dd, J=6.9, 3.9 Hz, 2H), 1.50 (dd, J=6.9, 3.9 Hz, 2H); MS 304.0 found 304.4 (M+H+) required.

Sources & evidence

ORD record
ord-faf544c1f5c6481896b3b98608504c86
Source dataset
uspto-grants-2007_11
Patent number
US07294640B2

Reaction notes

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