Ammonia → 2-Amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine

HRID 1591451ノート

反応式

HRID 1591451 の反応式
[NH3:1].Cl[CH:3]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4]1>C(Cl)Cl>[NH2:1][CH:3]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4]1

参加物

4

反応物 2

HCID 222AmmoniaHCID 122185992H-1,4-Benzothiazin-3(4H)-one, 2-chloro-

生成物 1

HCID 107974522-Amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Anhydrous ammonia gas was bubbled for one hour through a suspension of 500 mg (2.5 mmol) of 2-chloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (prepared by the method of Worley, et al; J. Org. Chem., 40, 1731-1734 (1975)) in 5 mL of methylene chloride. The mixture was filtered through Celite and the filtrate evaporated under vacuum. The residue was triturated with 20 mL of chloroform, filtered and the filtrate evaporated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 185 mg (1.0 mmol, 41%) of the product. 1H NMR (200 MHz, CDCl3): 2.00 (br s,2H), 4.68 (br s,1H), 6.9-7.4 (m,4H), 9.05 (br s,1H). FAB-MS: calculated for C8H8N2OS 180; found 181 (M+H,54%).

後処理

  1. customprepared by the method of Worley, et al
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate evaporated under vacuum
  4. customThe residue was triturated with 20 mL of chloroform
  5. filtrationfiltered
  6. customthe filtrate evaporated under vacuum
  7. customPurification by flash chromatography on silica
  8. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-f34e9671558b45beab8c900bbd8b7e62
出典データセット
uspto-grants-1993_04
特許番号
US05206235

反応ノート

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