Water → 3-[3-(2-Bromo-2-ethylthioethoxycarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978855Notes

Reaction equation

HRID 1978855 reaction equation
[Br:1][C:2]([C:24](Cl)=[O:25])=[CH:3][C:4]1[CH:5]=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])[CH:7]=[CH:8][C:9]=1[Cl:10].[CH2:27]([S:29][CH2:30][CH2:31][OH:32])[CH3:28].C(N(CC)CC)C.O>O1CCCC1>[Br:1][C:2]([C:24]([O:32][CH2:31][CH2:30][S:29][CH2:27][CH3:28])=[O:25])=[CH:3][C:4]1[CH:5]=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 962WaterHCID 80752-(Ethylthio)ethanolHCID 8471TriethylamineHCID 865837993-[3-(2-Bromo-2-chlorocarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Product 1

HCID 865837983-[3-(2-Bromo-2-ethylthioethoxycarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.36 g of 3-[3-(2-bromo-2-chlorocarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 20 ml of tetrahydrofuran were added dropwise to a solution of 0.58 g of 2-ethylmercaptoethanol and 0.56 g of triethylamine in 30 ml of tetrahydrofuran, and stirring was carried out for 5 hours. 100 ml of water were added and the aqueous phase was extracted with twice 100 ml of dichloromethane. The combined organic phases were washed three times with water, dried with sodium sulfate and evaporated down. The solid residue was stirred with diisopropyl ether, removed, washed with diisopropyl ether and petroleum ether and dried.

Workup

  1. extractionthe aqueous phase was extracted with twice 100 ml of dichloromethane
  2. washThe combined organic phases were washed three times with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated down
  5. stirringThe solid residue was stirred with diisopropyl ether
  6. customremoved
  7. washwashed with diisopropyl ether and petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-cc4257661da0442fb7525e87e0e8f1a6
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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