Triethylamine → 2-(Methylthio)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid Phenyl Ester

HRID 2053630Notes

Reaction equation

HRID 2053630 reaction equation
I.[C:2]1([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:11][C:10]([S:19][CH3:20])=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>CN(C)C1C=CN=CC=1.ClCCl>[C:32]1([O:31][C:29]([N:9]2[C@H:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:11]=[C:10]2[S:19][CH3:20])=[O:30])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 68569083cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide

Product 1

HCID 596554592-(Methylthio)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid Phenyl EsterYield 59.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(methylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydroiodide (42) (1.00 mg, 2.52 mmol), triethylamine (0.528 mL, 0.379 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (20 mL) is added phenyl chloroformate (0.379 mL, 3.02 mmol), and the mixture is stirred at rt overnight. The reaction mixture is diluted with dichloromethane and washed with water, brine, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane: EtOAc (70:30-60:40) gives 0.58 g of the product 548. 1H NMR (CDCl3) δ 7.25-6.95 (m, 11H), 6.95-6.80 (m, 2H), 6.80-6.70 (m, 2H), 5.80-5.65 (m, 2H), 2.62 (s, 3H). MS: m/z 389 (M++1).

Workup

  1. washwashed with water, brine
  2. dry with materialthe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel
  6. washgradient elution with heptane: EtOAc (70:30-60:40)

Sources & evidence

ORD record
ord-3c1cc70a1c124041b7ce5b6b5949eb07
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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