Methanol → HCID 178507232, compound

HRID 865106Notes

Reaction equation

HRID 865106 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[S:8][C:9]3[CH2:19][CH2:18][C:17]4[C:12](=[CH:13][C:14]([N+:20]([O-])=O)=[CH:15][CH:16]=4)[C:10]=3[N:11]=2)[N:3]=[CH:2]1.CO.[H][H]>[Ni].O1CCOCC1>[NH2:20][C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][CH2:19][C:9]3[S:8][C:7]([CH2:6][C:4]4[N:3]=[CH:2][NH:1][CH:5]=4)=[N:11][C:10]=32)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 178418361HCID 178418361, compoundHCID 1785264332-(4-Imidazolylmethyl)-8-nitro-4,5-dihydronaphtho[1,2-d]thiazole

Product 1

HCID 178507232HCID 178507232, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

5.0 g of Raney nickel (wet) was added to a solution of 0.52 g of.2-(4-imidazolylmethyl)-8-nitro-4,5-dihydronaphtho[1,2-d]thiazole obtained in Example 23 in 1,4-dioxane (40 ml)-methanol (20 ml), and the mixture was stirred for 2 hours in an atmosphere of hydrogen (1 atm). After filtration of insoluble matter, the solvent was evaporated from the filtrate, and the residue was mixed with ethyl acetate to effect crystallization. The resultant crude crystals were washed with hot ethyl acetate to afford 0.27 g (57%) of 8-amino-2-(4-imidazolylmethyl)-4,5-dihydronaphtho[1,2-d]thiazole.

Workup

  1. filtrationAfter filtration of insoluble matter
  2. customthe solvent was evaporated from the filtrate
  3. additionthe residue was mixed with ethyl acetate
  4. customcrystallization
  5. washThe resultant crude crystals were washed with hot ethyl acetate

Sources & evidence

ORD record
ord-e1444e0938434e02952d98b237d44915
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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