Histamine → HCID 178420852, compound

HRID 726241

Reaction equation

HRID 726241 reaction equation
[CH:1]1[N:5]=[CH:4][NH:3][C:2]=1[CH2:6][CH2:7][NH2:8].Br[C:10]1[S:11][CH:12]=[CH:13][N:14]=1.C(O)(=O)C(O)=O.CCOCC>CC(O)C.C(O)C>[NH:5]1[CH:1]=[C:2]([CH2:6][CH2:7][NH:8][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[N:3]=[CH:4]1

Participants

7

Reactant 4

HCID 774HistamineHCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 764302-Bromothiazole

Product 1

HCID 178420852HCID 178420852, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

1.1 g (10 mmol) of histamine base and 1.6 g (10 mmol) of 2-bromothiazole are brought to reflux in 15 ml of 2-propanol for 96 h. The reaction mixture is concentrated under reduced pressure until an oily residue is obtained which is chromatographed on a column of silica gel with a mixture of chloroform and methanol (1, 5 and 20%) as eluent to provide an oil. The latter is taken up in absolute ethanol and is treated with oxalic acid (2 molar equivalents). Addition of ether gives the title compound in the dioxalate form which, after having been crystallized from 2-propanol, melts at 198°-199° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure until an oily residue
  2. customis obtained which
  3. customis chromatographed on a column of silica gel with a mixture of chloroform and methanol (1, 5 and 20%) as eluent
  4. customto provide an oil

Sources & evidence

ORD record
ord-738ccf9741894fceb21b27e96f8d0f69
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Linked notes

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