Toluene → HCID 13497235, compound

HRID 1939715Notes

Reaction equation

HRID 1939715 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([N:12](C(C)C)[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH:22]([NH:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].[OH-].[Na+].[C:31]1(C)[CH:36]=CC=C[CH:32]=1>O>[CH:6]1([N:12]=[C:13]([N:15]([CH:16]([CH3:17])[CH3:18])[CH:31]([CH3:36])[CH3:32])[N:25]([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 7912DiisopropylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 70129448HCID 70129448, compound

Product 1

HCID 13497235HCID 13497235, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Phosphorus oxychloride (96 ml, 1.03 mol) is added dropwise over 30 min period to a toluene (800 ml) solution of cyclohexyl-diisopropylurea (226 g, 1.0 mol). The reaction is stirred 3.5 hours at 50° C., then stirred overnight at room temperature. Diisopropylamine (310 ml, 2.18 mol) is added to the reaction mixture dropwise for over a 2 hour period, then stirred 2 hours at room temperature. The reaction mixture is poured into water (2000 ml). The water layer is extracted with toluene (3×150 ml) and the toluene layer is discarded. Sodium hydroxide (240 g, 6 mol) is slowly added to the aqueous layer in an ice-water bath. Two layers formed and the aqueous layer is extracted with diethylether (2×150 ml). The organic layer and the extracts are combined and dried over Na2 CO3, filtered and concentrated. The residue is further distilled under vacuum (ca. 0.3-0.5 torr) collecting product, cyclohexyl-tetraisopropylguanidine, at 140°-143° C. (250g, 80%) of 99% purity as judged by gas chromatography. 1H NMR (CDCl3) δ 3.75-3.9(m, 1H), 3.37(m, 1H), 3.22-3.31 (m,1H), 1.12-1.77 (m, 10H), 1.22 (d, 6H), 1.14 (d, 6H) ppm.

Workup

  1. stirringstirred overnight at room temperature
  2. stirringstirred 2 hours at room temperature
  3. extractionThe water layer is extracted with toluene (3×150 ml)
  4. customTwo layers formed
  5. extractionthe aqueous layer is extracted with diethylether (2×150 ml)
  6. customdried over Na2 CO3
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationThe residue is further distilled under vacuum (ca. 0.3-0.5 torr)
  10. customcollecting product, cyclohexyl-tetraisopropylguanidine
  11. customat 140°-143° C.

Sources & evidence

ORD record
ord-0f548aa9da62491cbfa8a52148eaff41
Source dataset
uspto-grants-1997_12
Patent number
US05696290

Reaction notes

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