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2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → 2-Phenyl-ethenesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide

HRID 965627
Notes
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Reaction equation

HRID 965627 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[K+].[C:17]1([CH:23]=[CH:24][S:25]([NH-:28])(=[O:27])=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.C(N(C(C)C)CC)(C)C.O.C(OCC)C>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:28][S:25]([CH:24]=[CH:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:26])=[O:27])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 219795694,6-Dichloro-5-(4-chlorophenyl)-pyrimidineHCID 74047229HCID 74047229, compound

Product 1

HCID 740472202-Phenyl-ethenesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amideYield 61.2%

Reagents, catalysts & solvents 4

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent
HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 6.50 g of 4,6-dichloro-5-(4-chlorophenyl)-pyrimidine and 9.43 g of 2-phenyl-ethenesulfonamide potassium salt (Referential Example 1c) in 50 ml of DMSO and 4.4 ml of diisopropyl-ethylamine was stirred at rt for 65 h. The mixture was diluted with 500 ml of water and 250 ml of diethyl ether and was vigorously stirred for 15 min. The suspension was acidified by adding 8.5 g of citric acid monohydrate and stirring was continued at 5° C. for 30 min. The precipitate was collected and washed with water. The crude product was crystallised from 2-propanol at 2-3° C. The crystals were collected, washed with cold 2-propanol and dried to give 6.23 g of 2-phenyl-ethenesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide as a white powder. LC-MS: tR=5.24 min, [M+H]+=405.89 (ES+), [M−H]−=403.92 (ES−).

Workup

  1. stirringstirring
  2. waitwas continued at 5° C. for 30 min
  3. customThe precipitate was collected
  4. washwashed with water
  5. customThe crude product was crystallised from 2-propanol at 2-3° C
  6. customThe crystals were collected
  7. washwashed with cold 2-propanol
  8. customdried

Sources & evidence

ORD record
ord-a5a9cc2c852f4e33bea2866a157a00dd
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951856B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes