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

HRID 1939650Notes

Reaction equation

HRID 1939650 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-27c290e49f7747dca0bdf7d69992de05
Source dataset
uspto-grants-1997_12
Patent number
US05696275

Reaction notes

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