Sodium Hydroxide → HCID 178484432, compound

HRID 1194322Notes

Reaction equation

HRID 1194322 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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15615543HCID 15615543, compoundHCID 178513045HCID 178513045, compound2×

Product 1

HCID 178484432HCID 178484432, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. additionA mixture of 2.6 g
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with acetone
  4. dissolutiondissolved in water
  5. customThe solution thus obtained
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60e623d036214959bb2984a47bd03ef1
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

Loading…