Cyclohexyl isocyanate → (2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-n-cyclohexylacetamide

HRID 448021Notes

Reaction equation

HRID 448021 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[CH:14]1([N:20]=[C:21]=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:21]([NH:20][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:22])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Product 1

HCID 24953908(2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-n-cyclohexylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 1A (123 mg, 0.4 mmol) and cyclohexyl isocyanate (63 mg, 0.5 mmol) in CH2Cl2 (20 mL) at 0° C. was added dropwise a solution of DBU (0.076 mL, 0.5 mmol) in CH2Cl2 (5 mL). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was washed sequentially with water, brine and dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (CH2Cl2-MeOH 9:1) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (t, J=7 Hz, 3H), 1.10 (m, 3H), 1.29 (m, 4H), 1.51 (m, 3H), 1.70 (m, 4H), 1.95 (s, 3H), 2.02 (s, 3H), 3.33 (m, 3H), 5.02 (s, 1H), 6.74 (br d, J=7 Hz, 1H); MS (ESI) m/z 309 (M+H)+. Anal calcd for C17H28N2OS.0.25H2O: C, 65.24; H, 9.18; N, 8.95. Found: C, 65.49; H, 9.30; N, 8.93.

Workup

  1. washThe mixture was washed sequentially with water, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (CH2Cl2-MeOH 9:1)

Sources & evidence

ORD record
ord-e90ba013808a4c50bc9eed498f86c19d
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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