Sulfuryl chloride → 5-Chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide

HRID 1688080Notes

Reaction equation

HRID 1688080 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([Cl:18])[N:12]=1)=[O:4].S(Cl)([Cl:23])(=O)=O>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([Cl:23])=[C:8]([CH3:19])[C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([Cl:18])[N:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 866340193-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide

Product 1

HCID 866340795-Chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamideYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cold solution of 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (0.105 g, 0.33 mmol) in methylene chloride (4 mL) was treated with sulfuryl chloride (33 μL). The mixture was stirred for 16 hours and concentrated. Chromatography on preparative TLC plate (hexanes/ethyl acetate/methanol (50:25:1)) gave 5-chloro-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (10.4 mg, 9%): 1H NMR (300 MHz, CDCl3) δ 9.9 (s, 1H), 8.33 (s, 1H), 5.82 (br, 1H), 3.05 (d, 3H), 2.22 (s, 3H); MS (m/e): 351.1 (M+1).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-bbcf03e2a15b4b2fbcb2edffeeaf8b25
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…