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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
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HRID 1939650 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-27c290e49f7747dca0bdf7d69992de05
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696275

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