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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
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HRID 965627 반응식
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
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참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide
용매
HCID 962Water용매
HCID 3283Diethyl Ether용매
HCID 81531Diisopropylethylamine용매

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-a5a9cc2c852f4e33bea2866a157a00dd
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06951856B2

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