Ethylene Glycol → 2-Phenyl-ethenesulfonic acid [5-(4-chloro-phenyl)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide
Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:11])=[O:10])[C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.[CH2:27]([OH:30])[CH2:28][OH:29]>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:3]2[C:4]([NH:8][S:9]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:11])=[O:10])=[N:5][CH:6]=[N:7][C:2]=2[O:29][CH2:28][CH2:27][OH:30])=[CH:21][CH:22]=1Participants
3
Conditions
- Temperature
- 110 °C
Procedure
6.20 g of 2-phenyl-ethenesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide was added to a solution of 7.65 g of potassium-tert.-butylate in 100 ml of ethylene glycol. The resulting solution was heated to 110° C. and stirred for 17 h. The ethylene glycol was evaporated under high vacuum and the remaining residue was treated with 250 ml of cold water. The suspension was acidified by adding 10 g of citric acid monohydrate and stirred at 0° C. for 15 min. The precipitate was collected, washed with water and dried to give 6.71 g of 2-phenyl-ethenesulfonic acid [5-(4-chloro-phenyl)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide as a white powder. LC-MS: tR=4.55 min, [M+H]+=432.00 (ES+), [M−H]−=429.98 (ES−).
Workup
- customThe ethylene glycol was evaporated under high vacuum
- additionthe remaining residue was treated with 250 ml of cold water
- additionby adding 10 g of citric acid monohydrate
- stirringstirred at 0° C. for 15 min
- customThe precipitate was collected
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-017c40dfc84e411da52b501b5cdef586
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951856B2
Reaction notes
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