Histamine → HCID 178433305, compound

HRID 866421Notes

Reaction equation

HRID 866421 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH:18]1[N:22]=[CH:21][NH:20][C:19]=1[CH2:23][CH2:24][NH2:25]>>[C:1]([NH:3][C:4]([NH:25][CH2:24][CH2:23][C:19]1[N:20]=[CH:21][NH:22][CH:18]=1)=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])#[N:2]

Participants

3

Reactant 2

HCID 774HistamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178433305HCID 178433305, compound

Procedure

A mixture of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)-ethyl]-S-methylisothiourea (8.07 g) and histamine base (3.36 g) was heated for 3 hours at 100° and then for 3 hours at 130°-140°. The product was chromatographed on a column of silica gel with ethyl acetate/isopropyl alcohol (5:1 ) as eluent and crystallised by slow evaporation from isopropyl alcohol. Recrystallisation from water afforded the title compound, m.p. 170°-171°. (Found: C, 50.3; H, 6.2; N, 33.5; S, 9.7% C14H20N8S requires: C, 50.6; H, 6.1; N, 33.3; S, 9.7%).

Workup

  1. temperaturewas heated for 3 hours at 100°
  2. customThe product was chromatographed on a column of silica gel with ethyl acetate/isopropyl alcohol (5:1 ) as eluent
  3. customcrystallised by slow evaporation from isopropyl alcohol
  4. customRecrystallisation from water

Sources & evidence

ORD record
ord-8d623a0535fe4c5f83a4ee925fa65dab
Source dataset
uspto-grants-1978_07
Patent number
US04098898

Reaction notes

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