Hydrochloric Acid → HCID 131717851, compound

HRID 1590290Notes

Reaction equation

HRID 1590290 reaction equation
[N+](C1C=C(C=C(C(=O)C)C(OC(C)(C)C)=O)C=CC=1)([O-])=O.[ClH:22].COC1C=CC(CSC(=N)N)=CC=1.C([O-])(=O)C.[Na+].Cl.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][S:51][C:52]2[NH:53][C:54]([CH3:74])=[C:55]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH:56]([C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([N+:64]([O-:66])=[O:65])[CH:59]=3)[N:57]=2)=[CH:46][CH:45]=1>CN(C)C=O.CCOCC.ClCCl.C(OCC)(=O)C>[ClH:22].[CH3:42][O:43][C:44]1[CH:45]=[CH:46][C:47]([CH2:50][S:51][C:52]2[NH:53][C:54]([CH3:74])=[C:55]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH:56]([C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([N+:64]([O-:66])=[O:65])[CH:59]=3)[N:57]=2)=[CH:48][CH:49]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 13885856(4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)HCID 56996553HCID 56996553, compoundHCID 131717852HCID 131717852, compound

Product 1

HCID 131717851HCID 131717851, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, 1,1-dimethylethyl ester (28 g., 96.12 mmole) in dimethylformamide (98 ml.) is treated with S-(4-methoxybenzyl)thiopseudourea, hydrochloride (22.37 g., 96.12 mmole) and sodium acetate (7.9 g., 96.12 mmole). The mixture is heated at 60° overnight, diluted with ether, and filtered to remove sodium chloride. The filtrate is washed with water (150 ml.), sodium bicarbonate (150 ml.), and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered, and stripped to give an oil. This oil is dissolved in dichloromethane (300 ml.) and treated with methanolic hydrochloric acid (1 eq., 96.12 mmole) to crystallize out 41.74 g. of product. A second crop of 2.77 g. is collected by reducing the volume of the mother liquor and cooling at 0° overnight to give a total of 44.51 g. of white solid 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1,1-dimethylethyl ester; m.p. 192°. TLC (silica gel; ethyl acetate:hexanes, 1:2 Rf =0.51.

Workup

  1. temperatureThe mixture is heated at 60° overnight
  2. filtrationfiltered
  3. customto remove sodium chloride
  4. washThe filtrate is washed with water (150 ml.), sodium bicarbonate (150 ml.), and brine
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto give an oil
  8. customto crystallize out 41.74 g
  9. customis collected
  10. temperaturecooling at 0° overnight
  11. customto give a total of 44.51 g

Sources & evidence

ORD record
ord-1b89d022723647dc95fd828ea636b79e
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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