Diethyl Ether → 2-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amide

HRID 965624Notes

Reaction equation

HRID 965624 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[K+].[C:26]1([CH:32]=[CH:33][S:34]([NH-:37])(=[O:36])=[O:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)C>CS(C)=O>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:37][S:34]([CH:33]=[CH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:35])=[O:36])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 74047229HCID 74047229, compound

Product 1

HCID 738818642-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amideYield 62.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 4,6-dichloro-5-p-tolyl-pyrimidine (2.0 g) disolved in DMSO (35 ml) was added di-isopropyl-ethyl-amine (1.46 ml) followed by 2-phenyl-ethenesulfonamide potassium salt (2.78 g). The mixture was stirred for 48 h at rt then poured onto water (500 ml) and diethylether (250 ml) was added and the solution was stirred for 30 minutes. The layers were separated and the water layer was acidified with acetic acid (2.0 ml) and cooled to 0° C. for 1 h. The precipitated product was filtered off and washed with water and diethylether and dried to give 2-phenyl-ethenesulfonic acid(6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (2.02 g). tR=5.32 (LC); M+=386.23 (ES+); M−=384.22 (ES−).

Workup

  1. additionwas added
  2. stirringthe solution was stirred for 30 minutes
  3. customThe layers were separated
  4. temperaturecooled to 0° C. for 1 h
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water and diethylether
  7. customdried

Sources & evidence

ORD record
ord-4194ace59e03460db986da8a14bb8414
Source dataset
uspto-grants-2005_10
Patent number
US06951856B2

Reaction notes

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