Water → 4-({4-[4-(Trifluoromethyl)phenyl]pyrimidin-2-yl}amino)benzenesulfonyl chloride

HRID 1715691Notes

Reaction equation

HRID 1715691 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Cl:25][S:26](O)(=[O:28])=[O:27]>>[F:21][C:20]([F:23])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:1]3[CH:2]=[CH:3][C:4]([S:26]([Cl:25])(=[O:28])=[O:27])=[CH:5][CH:6]=3)[N:13]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 57446828N-phenyl-4-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine

Product 1

HCID 866042824-({4-[4-(Trifluoromethyl)phenyl]pyrimidin-2-yl}amino)benzenesulfonyl chloride

Procedure

A solution of N-phenyl-4-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine (0.16 g, 0.5 mmol) in 1.5 ml of chlorosulfonic acid is stirred at 65 to 70° C. for 1 hr. It is then cooled to room temperature, and added slowly to a stirred mixture of ice and water. The resulting suspension is filtered, and the precipitate is washed with water and then dried in vacuo to give 0.24 g of a yellow solid; mp 186-188° C.; HRMS: calcd for C17H11ClF3N3O2S, 413.0213; found (ESI-FTMS, [M+H]1+), 414.02984.

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe precipitate is washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0c017506cd7d4add8613e67c5da0f2f4
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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