Triethylamine → alpha-Pivaloyl-alpha-(1-benzyl-5-(2-hydroxyethoxy)hydantoin-3-yl)-2-chloroacetanilide

HRID 1886308Notes

Reaction equation

HRID 1886308 reaction equation
[CH2:1]([N:8]1[CH:14]([O:15][CH2:16][CH2:17][OH:18])[C:12](=[O:13])[NH:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[C:27]([C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])([Cl:37])[C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C(Cl)Cl>[C:38]([C:27]([N:11]1[C:12](=[O:13])[CH:14]([O:15][CH2:16][CH2:17][OH:18])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:10])([Cl:37])[C:28]([NH:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:29])(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19875675alpha-Bromo-2-pivaloyl-2-chloroacetanilideHCID 198756771-Benzyl-5-(2-hydroxyethoxy)hydantoin

Product 1

HCID 19875676alpha-Pivaloyl-alpha-(1-benzyl-5-(2-hydroxyethoxy)hydantoin-3-yl)-2-chloroacetanilideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

51.5 g of 1-benzyl-5-(2-hydroxyethoxy)hydantoin and 20 g of triethylamine were dissolved in 500 ml of methylene chloride, and a solution of 34.8 g of α-bromo-α-pivaloyl-2-chloroacetanilide in 200 ml of methylene chloride was dropwise added thereto in about 1 hour. After completion of the dropwise addition, the solution was stirred for 2 hours. Then, the reaction solution was washed twice with 300 ml of dilute hydrochloric acid, and twice with 300 ml of water. After drying the reaction solution with sodium sulfate, it was concentrated and purified by silica gel chromatography to obtain 42.2 g of oily α-pivaloyl-α-(1-benzyl-5-(2-hydroxyethoxy)hydantoin-3-yl)-2-chloroacetanilide. (Yield: 84%)

Workup

  1. additionAfter completion of the dropwise addition
  2. washThen, the reaction solution was washed twice with 300 ml of dilute hydrochloric acid
  3. dry with materialAfter drying the reaction solution with sodium sulfate, it
  4. concentrationwas concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0fc41d387b2545538bbb81422a745e05
Source dataset
uspto-grants-1992_09
Patent number
US05151356

Reaction notes

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