Hydrochloric Acid → HCID 19919854, compound

HRID 1648514Notes

Reaction equation

HRID 1648514 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[C:7](/[CH:10]=[C:11]2\[NH:12][C:13](=[O:20])[N:14]([CH2:17][O:18][CH3:19])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[ClH:38].[Cl:39][CH2:40][C:41]1[N:42]=[C:43]([CH3:46])[S:44][CH:45]=1.Cl>CN(C=O)C.C(OCC)(=O)C.CCOCC>[ClH:39].[ClH:38].[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:40][C:41]3[N:42]=[C:43]([CH3:46])[S:44][CH:45]=3)[C:13](=[O:20])[N:14]([CH2:17][O:18][CH3:19])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 19919787HCID 19919787, compound

Product 1

HCID 19919854HCID 19919854, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[[1-(methoxymethyl)-2,5-dioxo-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate (0.307 g, 0.721 mmol) in DMF (4 mL) is added K2CO3 (0.500 g, 3.62 mmol). After stirring for 5 minutes 4-chloromethyl-2-methylthiazole hydrochloride (0.265 g, 1.44 mmol) is added. The mixture is stirred for 48 hours. A pale brown slurry results which was diluted with ethyl acetate and washed with water and brine and then dried over MgSO4. Chromatography eluting with 1% methanol in chloroform and evaporation in vacuo affords a viscous oil. This oil is dissolved in ether and treated with ethereal HCl to afford a foamy solid upon evaporation in vacuo. This solid is crystallized from 2-propanol/ether.

Workup

  1. additionis added
  2. customA pale brown slurry results which
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. washChromatography eluting with 1% methanol in chloroform and evaporation in vacuo
  6. customaffords a viscous oil
  7. customto afford a foamy solid
  8. customupon evaporation in vacuo
  9. customThis solid is crystallized from 2-propanol/ether

Sources & evidence

ORD record
ord-22f35ec79f5643be8d8f3ac7eadde6f6
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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