2-Benzylsulfanyl-4,5-dihydro-1H-imidazole → HCID 178439433, compound

HRID 485607Notes

Reaction equation

HRID 485607 reaction equation
C(S[C:9]1[NH:10][CH2:11][CH2:12][N:13]=1)C1C=CC=CC=1.[CH3:14][CH:15]([CH:17]1[CH2:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[CH2:18]1)[CH3:16]>ClCCl.C1N2CCN(CC2)C1>[CH3:16][CH:15]([CH:17]1[CH2:18][C:19](=[O:24])[C:20](=[C:9]2[NH:13][CH2:12][CH2:11][NH:10]2)[C:21](=[O:23])[CH2:22]1)[CH3:14]

Participants

5

Reactant 2

HCID 4097802-Benzylsulfanyl-4,5-dihydro-1H-imidazoleHCID 5661065-(Isopropyl)cyclohexane-1,3-dione

Product 1

HCID 178439433HCID 178439433, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-benzylthio-4,5-dihydro-1H-imidazole (15.4 grams, 0.08 mole), 5-(1-methylethyl)-1,3-cyclohexanedione (12.3 grams, 0.08 mole) and 0.11 gram of DABCO is heated at 115°-120° C., with stirring, for a period of 7.1 hours. The cooled residue is dissolved in dichloromethane and the solution extracted with three portions of 3N sodium hydroxide, then with four portions of 3N hydrochloric acid. The organic phase is then dried over magnesium sulfate and evaporated, to give 15.31 grams of crude product as a yellow solid. The material is recrystallized twice from toluene and once from ethyl acetate, to give 2.58 grams of product, m.p. 223°-225° C.

Workup

  1. temperatureis heated at 115°-120° C.
  2. extractionthe solution extracted with three portions of 3N sodium hydroxide
  3. dry with materialThe organic phase is then dried over magnesium sulfate
  4. customevaporated
  5. customto give 15.31 grams of crude product as a yellow solid
  6. customThe material is recrystallized twice from toluene and once from ethyl acetate

Sources & evidence

ORD record
ord-b5beacc181e94ebf82c448123e14ebec
Source dataset
uspto-grants-1985_08
Patent number
US04537616

Reaction notes

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