Hydrochloric Acid → HCID 9960720, compound

HRID 1648517Notes

Reaction equation

HRID 1648517 reaction equation
[ClH:1].[CH2:2]([C:6]1[N:7]([CH2:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[C:8](/[CH:11]=[C:12]2\[NH:13][C:14](=[O:22])[N:15]([CH2:18][CH2:19][CH2:20][CH3:21])[C:16]\2=[O:17])=[CH:9][N:10]=1)[CH2:3][CH2:4][CH3:5].C([O-])([O-])=O.[K+].[K+].Cl.[CH3:41][C:42]1[S:43][CH:44]=[C:45]([CH2:47][Cl:48])[N:46]=1.Cl>CN(C=O)C.CCOCC>[ClH:48].[ClH:1].[CH2:2]([C:6]1[N:7]([CH2:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[C:8](/[CH:11]=[C:12]2\[N:13]([CH2:47][C:45]3[N:46]=[C:42]([CH3:41])[S:43][CH:44]=3)[C:14](=[O:22])[N:15]([CH2:18][CH2:19][CH2:20][CH3:21])[C:16]\2=[O:17])=[CH:9][N:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 19919808HCID 19919808, compound

Product 1

HCID 9960720HCID 9960720, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[(1-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl]benzoate hydrochloride (0.474 g, 1.0 mmol) in DMF (5 mL) is added K2CO3 (2.0 g, 15 mmol). After stirring for 5 minutes 2-methyl-4-(chloromethyl)thiazole hydrochloride (0.184 g, 1.0 mmol) is added. An additional amount of DMF (10 mL) is added after stirring for 30 minutes. The mixture is stirred for 5 days and then filtered. The filtrate is concentrated in vacuo and dissolved in ether (50 mL). This solution is washed with water and dried over K2CO3 and charcoal. A viscous oil is obtained by evaporation of the solvents in vacuo which is dissolved in ether and treated with ethereal HCl and then evaporated in vacuo to afford a solid foam. Recrystallized from 2-propanol/ether. Anal. Calcd. for C29H35N5O4S. 2HCl.0.5 H2O: C, 55.14; H, 6.07; N, 11.08

Workup

  1. additionis added
  2. stirringThe mixture is stirred for 5 days
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutiondissolved in ether (50 mL)
  6. washThis solution is washed with water
  7. dry with materialdried over K2CO3 and charcoal
  8. customA viscous oil is obtained by evaporation of the solvents in vacuo which
  9. customevaporated in vacuo
  10. customto afford a solid foam
  11. customRecrystallized from 2-propanol/ether

Sources & evidence

ORD record
ord-4a3cca43671746d88297be75558088fa
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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