Histamine → HCID 178420852, compound

HRID 744049Notes

Reaction equation

HRID 744049 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-e146cc43908f45f38f68f1c9a8a4e603
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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