Undecanoic Acid → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethyl undecanoate

HRID 1005562

Reaction equation

HRID 1005562 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][CH2:17][OH:18])=[N:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:22](O)(=[O:33])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N=C=NCCCCCC)CCCCC>C(Cl)Cl>[C:22]([O:18][CH2:17][CH2:16][C:13]1[N:14]([CH3:15])[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:19]([CH3:21])[CH3:20])[N:12]=1)(=[O:33])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8180Undecanoic AcidHCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanolHCID 139457471,3-Dihexylcarbodiimide

Product 1

HCID 696871235-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethyl undecanoateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 22 (345 mg, 1 mmol), undecanoic acid (186 mg, 1 mmol) and N,N-dimethylaminopyridine (122 mg, 1 mmol) in methylene chloride (3 mL) was added 1,3-dihexylcarbodiimide (206 mg, 1 mmol) under ice-cooling, and stirred at room temperature overnight. The precipitated insoluble matter was filtered, and the filtrate was concentrated. The residue was purified by chromatography on a silica gel column (hexane - ethyl acetate (1:1)) to give the compound 106 (461 mg, 90%) as oil. Rf 0.50 (1:1 EtOAc - hexane). 1H-NMR (CDCl3): δH0.88 (3 H, S, t-like, CH3), 1.23 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.25 (14 H, bs, --CH2 --), 3.09 (1 H, sep, J 6.9 Hz, (CH3)2CH), 3.10 (2 H, t, J 7.2 Hz, CH2), 3.49 (3 H, s, NCH3), 4.42 (2 H, t, J 7.2 Hz), 6.80 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 7.11 (1 H, t, J 1.8 Hz, arom 4-H) Elementary analysis (for C26H38N2O2SCl2) Calcd. : C, 60.81% H, 7.46% N, 5.45% S, 6.24% Cl, 13.81% Found: C, 60.55% H, 7.39% N, 5.54% S, 6.14% Cl, 13.81%

Workup

  1. temperaturecooling
  2. filtrationThe precipitated insoluble matter was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography on a silica gel column (hexane - ethyl acetate (1:1))

Sources & evidence

ORD record
ord-e2a7db7e92bb4a2c8b5c3122d9225811
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

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