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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
ノート
印刷プレビュー

反応式

HRID 965627 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒
HCID 962Water溶媒
HCID 3283Diethyl Ether溶媒
HCID 81531Diisopropylethylamine溶媒

実験手順

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−).

後処理

  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

出典と根拠

ORDレコード
ord-a5a9cc2c852f4e33bea2866a157a00dd
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06951856B2

反応ノート

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