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Dimethyl Sulfoxide → N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamide

HRID 411112
ノート
印刷プレビュー

反応式

HRID 411112 の反応式
[NH2:1][C:2]1[N:14]=[C:5]2[N:6]=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.CS(C)=O>C(#N)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=[C:2]([NH:1][S:23]([C:17]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=3[Cl:15])(=[O:25])=[O:24])[N:14]=[C:5]2[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-

生成物 1

HCID 12056874N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamide収率 92%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]-pyrimidine (0.75 g, 3.8 mmol) and 2,6-dichlorobenzene-sulfonyl chloride (1.86 g, 7.6 mmol) were mixed in dry acetonitrile (15 mL). To this mixture was added dry pyridine (0.61 mL) and dry DMSO (54 μL, 0.7 mmol). The mixture was allowed to stir at room temperature. After 24 hours, the solvent was removed in vacuo, the residue was partitioned between CH2Cl2 (300 mL) and 2N HCl and the solids were collected by vacuum filtration to give a white solid A. The CH2Cl2 was dried (MgSO4) and removed in vacuo to give a white solid B. Both HPLC and NMR indicated that solid A and B are product. The solids were combined to afford the product as a white powder (1.41 g, 92%). mp 211-213° C. Anal: Cacld for C13H11Cl2N5O4S: C, 38.63; H, 2.74; N, 17.33; S, 7.93; found: C, 38.11; H, 2.68; N, 16.83; S, 7.77. 1H NMR (DMSO-d6): δ 12.4 (bs, 1H); 7.64-7.54 (m, 3H); 6.26 (s, 1H); 4.07 (s, 3H); 3.88 (s, 3H).

後処理

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 (300 mL) and 2N HCl
  3. filtrationthe solids were collected by vacuum filtration
  4. customto give a white solid A
  5. dry with materialThe CH2Cl2 was dried (MgSO4)
  6. customremoved in vacuo
  7. customto give a white solid B

出典と根拠

ORDレコード
ord-d29b6c1a44644505b2ad52edf33606bb
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06559101B2

反応ノート

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