Sodium Hydroxide → HCID 178484432, compound

Reaction equation

[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[O:6][C:7]([C:10](=O)[CH2:11]Br)=[CH:8][CH:9]=1)=[O:4].[C:15]([NH:18][C:19]([NH2:21])=[S:20])(=[NH:17])[NH2:16].[OH-].[Na+]>CC(C)=O>[NH:18]([C:19]1[S:20][CH:11]=[C:10]([C:7]2[O:6][C:5]([C:3](=[O:4])[N:2]([CH3:14])[CH3:1])=[CH:9][CH:8]=2)[N:21]=1)[C:15]([NH2:17])=[NH:16]

Participants

Procedure

A mixture of 2.6 g. (0.01 mole) of N,N-dimethyl5-(2-bromoacetyl)furan-2-carboxamide, 1.18 g. (0.01 mole) of guanylthiourea and 100 ml. of acetone was stirred at room temperature for 4 hours. An additional 354 mg. of guanylthiourea was added and stirring was continued for 3 days. The reaction mixture was filtered, and the residue was washed with acetone and then dissolved in water. The solution thus obtained was made alkaline using 10% sodium hydroxide solution and extracted with ethyl acetate. The extracts were dried (MgSO4) and concentrated in vacuo to give a first crop of the title compound (500 mg.). The aqueous phase from the extraction was further basified (to pH 14) and extracted with n-butanol. Evaporation of the n-butanol gave a second crop of the title compound (900 mg.). The two crops of the title compound were combined and recrystallized from aqueous ethanol, giving 550 mg. of a brown solid, mp. 252°-253.5° C. (dec). Two additional samples of the title compound were obtained from the recrystallization mother liquors: 190 mg. mp 249°-252° C.; 91 mg., mp 248°-251° C.