Azobisisobutyronitrile → 4-(Bromomethyl)-2-(4-chlorophenyl)thiazole-5-carboxylic acid

HRID 1799796Notes

Reaction equation

HRID 1799796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.C[Si](N[Si](C)(C)C)(C)C.C1C(=O)N([Br:33])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:33][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[S:9][C:10]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 13838HexamethyldisilazaneHCID 67184N-bromobutanimideHCID 27686792-(4-Chlorophenyl)-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 583877234-(Bromomethyl)-2-(4-chlorophenyl)thiazole-5-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Following the procedure described in Part D of Example 1, 1.00 g of commercially available of 2-(4-chlorophenyl)-4-methylthiazole-5-carboxylic acid, 0.502 mL of HMDS, 0.702 g of NBS and 32 mg of AIBN in 3.40 mL of CCl4 afforded the title compound (0.940 g, 72% yield) as a yellow/orange solid: 1H NMR (500 MHz, DMSO-d6) δ 11.06 (1H, br. s.), 8.02 (2H, d, J=8.25 Hz), 7.61 (2H, d, J=8.80 Hz), 5.01 (2H, s); HPLC retention time: 3.591 min; LCMS (ES): m/z 334 [M+H]+.

Sources & evidence

ORD record
ord-2f75b75d3b094ff5b1c7407c8b8ec08d
Source dataset
uspto-grants-2013_01
Patent number
US08344160B2

Reaction notes

Loading…