1,4-Dibromo-2,2-diethoxy-3-butanone → HCID 178467676, compound

HRID 280732

Reaction equation

HRID 280732 reaction equation
[Br:1][CH2:2][C:3]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[C:4](=O)[CH2:5]Br.[C:14]([NH:17][C:18]([NH2:20])=[S:19])(=[NH:16])[NH2:15]>O1CCCC1>[CH4:2].[NH:17]([C:18]1[S:19][CH:5]=[C:4]([C:3]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[CH2:2][Br:1])[N:20]=1)[C:14]([NH2:16])=[NH:15]

Participants

5

Reactant 2

HCID 131009731,4-Dibromo-2,2-diethoxy-3-butanoneHCID 178513045HCID 178513045, compound

Product 2

HCID 297MethaneHCID 178467676HCID 178467676, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25.5 g (80 mmol) of 1,4-dibromo-2,2-diethoxy-3-butanone, 11.8 g (100 mmol) of N-amidinothiourea, and 150 ml of tetrahydrofuran was heated at reflux for 3 hours. The mixture was filtered to remove some insoluble solid, and the filtrate was concentrated. The residue was triturated with 200 ml of saturated sodium bicarbonate, then extracted four times with a total of 500 ml of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and evaporated leaving a solid. Recrystallization from 250 ml of acetonitrile, after decolorization with charcoal, afforded 9.7 g (36%) of 2-guanidino-4-(2-bromo-1,1-diethoxyethyl)thiazole as a white solid, mp 157°-158°; calcd. for C10H17N4O2SBr: C, 35.62; H, 5.08; N, 16.61; Br, 23.69; S, 9.51; found: C, 35.60; H, 4.97; N, 16.99; Br, 23.75; S, 9.59.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. customto remove some insoluble solid
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with 200 ml of saturated sodium bicarbonate
  7. extractionextracted four times with a total of 500 ml of ethyl acetate
  8. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customleaving a solid
  12. customRecrystallization from 250 ml of acetonitrile

Sources & evidence

ORD record
ord-f3ffcaeabb7f4ad9ac8cf42c953eed67
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Linked notes

Loading…