Chloroform methanol → HCID 178512613, compound

HRID 66580Notes

Reaction equation

HRID 66580 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]3[C:20](=O)[C:19](=[O:22])[C:18]=3[O:23]C)[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].CO.C(Cl)(Cl)Cl.[NH:31]([C:35]1[S:36][CH:37]=[C:38]([CH:40]2[CH2:45][CH2:44][CH2:43][CH:42]([NH2:46])[CH2:41]2)[N:39]=1)[C:32]([NH2:34])=[NH:33]>CO>[NH:31]([C:35]1[S:36][CH:37]=[C:38]([CH:40]2[CH2:45][CH2:44][CH2:43][CH:42]([NH:46][C:20]3[C:19](=[O:22])[C:18](=[O:23])[C:17]=3[NH:16][CH:12]3[CH2:13][CH2:14][CH2:15][CH:10]([C:8]4[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=4)[CH2:11]3)[CH2:41]2)[N:39]=1)[C:32]([NH2:34])=[NH:33]

Participants

5

Reactant 3

HCID 21584188Chloroform methanolHCID 178493670HCID 178493670, compoundHCID 1785126122-Guanidino-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 178512613HCID 178512613, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[3-(2-guanidinothiazol-4-yl)cyclohexylamino]-2-methoxycyclobutene-3,4-dione (0.1 g.) in 15 ml. of methanol/chloroform (50:50 v/v) was added a solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.07 g.) in methanol (3 ml.) and the resulting solution was allowed to stand at room temperature for 6 hours. After heating under reflux for 6 hours, the reaction mixture was concentrated and cooled to give, as a white amorphous solid, 1,2-bis[3-(2-guanidinothiazol-4-yl)cyclohexylamino]cyclobutene-3,4-dione. The carbon-13 magnetic resonance spectrum (δ relative to tetramethylsilane) in d6DMSO included one carbon singlets at 181.9, 175.0 167.0, 156.8, 155.4, 100.3, 52.4 and a series of signals from 52.4 to 24.1 (including resonances attributable to solvent) p.p.m.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 6 hours
  3. concentrationthe reaction mixture was concentrated
  4. temperaturecooled

Sources & evidence

ORD record
ord-e5d36c8635d848f5afc9e14c4790c06c
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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