Hydrochloric Acid → HCID 86583792, compound

HRID 1978844Notes

Reaction equation

HRID 1978844 reaction equation
[CH3:1][CH2:2]CC[O-].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[CH:10][C:9]=1[CH:27]=[C:28]([Cl:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl.O>C(O)CCC>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[CH:10][C:9]=1[CH:27]=[C:28]([Cl:34])[C:29]([O:31][CH2:32][CH2:33][CH2:1][CH3:2])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23669364Sodium n-butylateHCID 86583793HCID 86583793, compound

Product 1

HCID 86583792HCID 86583792, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

50 ml of a sodium n-butylate solution in n-butanol (prepared from 0.3 g of 80% strength sodium hydride and 50 ml of n-butanol) were added to a solution of 4.4 g of 3-[4-chloro-3-(2-chloro-2-ethoxycarbonylethen-1-yl)-phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 50 ml of n-butanol, and stirring was carried out for 5 hours at room temperature. Thereafter, the mixture was neutralized with 10% strength hydrochloric acid at 0-5° C. and the resulting solution was stirred into 100 ml of water at 0-5° C. The aqueous phase was extracted with 100 ml of toluene, and the combined organic phases were washed with three times 50 ml of water, dried over sodium sulfate and evaporated down. The oil obtained was chromatographed over silica gel (dichloromethane), and the oil obtained therefrom was stirred with petroleum ether. The resulting solid was filtered off, washed with petroleum ether and dried.

Workup

  1. extractionThe aqueous phase was extracted with 100 ml of toluene
  2. washthe combined organic phases were washed with three times 50 ml of water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down
  5. customThe oil obtained
  6. customwas chromatographed over silica gel (dichloromethane)
  7. customthe oil obtained
  8. filtrationThe resulting solid was filtered off
  9. washwashed with petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-0b417f1964cd40228f228458c47e57ad
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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