5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 178483230, compound

HRID 1446989Notes

Reaction equation

HRID 1446989 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]([NH:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:24][N:25]([CH2:27][C:28]1[O:32][C:31]([CH2:33][S:34][CH2:35][CH2:36][NH2:37])=[CH:30][CH:29]=1)[CH3:26]>>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[C:12]([NH:16][C:17]([NH:37][CH2:36][CH2:35][S:34][CH2:33][C:31]3[O:32][C:28]([CH2:27][N:25]([CH3:26])[CH3:24])=[CH:29][CH:30]=3)=[CH:18][N+:19]([O-:21])=[O:20])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

3

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 178503819HCID 178503819, compound

Product 1

HCID 178483230HCID 178483230, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[3-(2-guanidinothiazol-4-yl)phenylamino]-1-methylthio-2-nitroethylene (0.16 g.) and 2-[(5-dimethylaminomethylfuran-2-yl)methylthio]ethylamine (1 g.) was heated at 100° C. for 2 hours. The product was extracted 10 times with 5 ml. portions of diethyl ether and the residual gum was applied to Merck 60 F254 preparative plates and eluted with ethyl acetate/methanol/concentrated aqueous ammonia 6:1:1 v/v/v. The solid obtained (0.05 g.) was crystallised twice from acetonitrile to give 1-[3-(2-guanidinothiazol-4-yl)phenylamino]-1-[2-[(5-dimethylaminomethylfuran-2-yl)methylthio]ethylamino]-2-nitroethylene, m.p. 175°-180° C. (decomp.).

Workup

  1. extractionThe product was extracted 10 times with 5 ml
  2. washeluted with ethyl acetate/methanol/concentrated aqueous ammonia 6:1:1 v/v/v
  3. customThe solid obtained (0.05 g.)
  4. customwas crystallised twice from acetonitrile

Sources & evidence

ORD record
ord-d78ab8d09900460ea41bf8eb2dbbecca
Source dataset
uspto-grants-1982_02
Patent number
US04315009

Reaction notes

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