Dimethylthiocarbamoyl chloride → HCID 25228497, compound

HRID 1920688Notes

Reaction equation

HRID 1920688 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[S:4].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH3:18])=[N:15]2)=[CH:10][CH:9]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:6])[C:3](=[S:4])[O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH3:18])=[N:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 27871Dimethylthiocarbamoyl chlorideHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 25228497HCID 25228497, compoundYield 147.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Referring now to FIG. 22, under nitrogen, dimethylthio-carbamoyl chloride (1.35 g, 10.95 mmol) and DMAP (1.33 g, 10.95 mmol) were added to a suspension of 4 (300.0 mg, 0.628 mmol) in CH2Cl2 (6 mL). The dark brown solution was stirred for 24 h before it was diluted with chloroform and purified by column chromatography (4:6 to 1:1 EtOAc/hexane) to provide 16 (299 mg, 0.929 mmol, 64%) as an off-white solid: 1H NMR (CDCl3) δ 8.05, (1H, d, J=8.4 Hz), 7.78 (1H, d, J=8.8 Hz), 7.67 (1H, d, J=2.4 Hz), 7.29 (1H, dd, J=8.0, 2.8 Hz), 7.27, (1H, dd, J=8.4, 3.6 Hz), 3.48 (3H, s), 3.40 (3H, s), 2.73 (3H, s); 13C NMR (CDCl3) δ 187.6, 159.9, 154.7, 148.6, 136.2, 128.3, 124.8, 122.7, 122.1, 120.9, 43.5, 39.1, 25.6; FTIR (neat) 3379, 2940, 1624, 1603, 1531, 1504, 1393, 1283, 1206, 1169, 1130, 843, 748 cm−1; MS (ESI) m/z calculated for (C13H14N2OS+H)+ 247, found 247; HRMS (ESI) m/z calculated for (C13H14N2OS+H)+ 247.0905, found 201.0900.

Workup

  1. custompurified by column chromatography (4:6 to 1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-0184830cc65e43e1a0f8fb98e56b8bf7
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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