Toluene → HCID 131720356, compound

HRID 1939714Notes

Reaction equation

HRID 1939714 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([N:12](CC)[C:13]([NH:15][CH2:16][CH3:17])=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH:20]([NH:23][CH:24]([CH3:26])[CH3:25])([CH3:22])C.[OH-].[Na+].[C:29]1(C)[CH:34]=CC=C[CH:30]=1>O>[CH:6]1([N:12]=[C:13]([N:15]([CH2:16][CH3:17])[CH:29]([CH3:34])[CH3:30])[N:23]([CH2:20][CH3:22])[CH:24]([CH3:26])[CH3:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 7912DiisopropylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21560115HCID 21560115, compound

Product 1

HCID 131720356HCID 131720356, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (78.2 g, 0.51 mol) is added dropwise over 1 hour period to a toluene (250 ml) solution of cyclohexyl-diethylurea (99 g, 0.5 mol). The reaction is stirred overnight at room temperature. Diisopropylamine (101 g, 1.0 mol). is added dropwise for over a 1 hour period, then stirred 2 hours at room temperature. The reaction mixture is poured into water (300 ml). The water layer is extracted with toluene (3×100 ml) and the toluene layers are discarded. Sodium hydroxide (120 g, 3 mol) is slowly added to the aqueous layer in an ice-water bath. Two layers formed and the aqueous layer is extracted with diethylether (2×100 ml). The organic layer and extracts are combined and dried over Na2CO3, filtered and concentrated. The residue is further distilled under vacuum (ca, 0.3-0.5 torr) collecting product, cyclohexyl-diethyl-diisopropylguanidine, at 137°-140° C. (95 g, 68%) of 99% purity as judged by gas chromatography. 1H NMR (CDCl3) δ 3.57 (m, 1H), 3.36 (m, 1H), 3.21 (q, 2H), 2.94 (q, 2H, 3.12 (m, 1H0, 2.93 (q, 2H), 1.13-1.77 (m, 10H), 1.20 (d, 6H), 1.12(d, 6H), 1.00 (t, 3H), 0.99 (t, 3H) ppm.

Workup

  1. additionis added dropwise for over a 1 hour period
  2. stirringstirred 2 hours at room temperature
  3. extractionThe water layer is extracted with toluene (3×100 ml)
  4. customTwo layers formed
  5. extractionthe aqueous layer is extracted with diethylether (2×100 ml)
  6. dry with materialdried over Na2CO3
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationThe residue is further distilled under vacuum (ca, 0.3-0.5 torr)
  10. customcollecting product, cyclohexyl-diethyl-diisopropylguanidine
  11. customat 137°-140° C.

Sources & evidence

ORD record
ord-b0388c66effd4ce086a44478c5f22b75
Source dataset
uspto-grants-1997_12
Patent number
US05696290

Reaction notes

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