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Hydrochloric Acid → (1E)-N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine

HRID 1939650
ノート
印刷プレビュー

反応式

HRID 1939650 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[CH3:15][NH:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20].Cl>O>[CH3:15][NH:16]/[C:17](/[NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[O:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=1)=[CH:18]\[N+:19]([O-:21])=[O:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 1235491-Methylthio-1-methylamino-2-nitroethyleneHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

生成物 1

HCID 3001055(1E)-N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine収率 90.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
10 °C

実験手順

2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (50 g) and N-methyl-1-(methylthio)-2-nitroetheneamine (40 g) in water (235 ml) was stirred and heated at 45°-50° C. The solution was stirred further for 3-4 hrs. It was acidified with hydrochloric acid and extracted with chloroform. The solution was basified with potassium carbonate and ranitidine base was separated. The water, if any, was removed by azeotropic distillation under reduced pressure at 40°-45° C. using isopropanol. The resultant solution was cooled to 10° C. and n-hexane (500 ml) was added. Ranitidine base was filtered off and dried under vacuum to give the crude product (66.2 g), m.p. 68°-70° C.; purity=99.4% (HPLC); IR(KBr): 3280, 3200, 2820, 2774, 1620, 1580, 1440, 1370, 1258, 1130, 1020, 990, 820, 790, 760, 680 and 600 cm-1 ; δH (CDCl3):2.23 [6H,s, --N(CH3)2 ], 2.75(2H, t, --SCH2CH2), 2.85(3H,br d, CH3NH--), 3.3 (2H,2t, --CH2NH--), 3.4(2H,s, >NCH2), 3.7 (2H,s, CH2 bridge linking), 6.0-6.2 (2H,AB,furan) and 6.5 (,1H,s,=CHNO2).

後処理

  1. temperatureheated at 45°-50° C
  2. extractionextracted with chloroform
  3. customwas separated
  4. customThe water, if any, was removed by azeotropic distillation under reduced pressure at 40°-45° C.
  5. additionn-hexane (500 ml) was added
  6. filtrationRanitidine base was filtered off
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-27c290e49f7747dca0bdf7d69992de05
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05696275

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート