Toluene → HCID 11807199, compound

HRID 1939713Notes

Reaction equation

HRID 1939713 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1(C)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:13]1([N:19]([CH2:25][CH3:26])[C:20]([NH:22]CC)=O)CCCC[CH2:14]1.[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28]>O>[CH:6]1([N:22]=[C:20]([N:19]([CH2:25][CH3:26])[CH2:13][CH3:14])[N:29]([CH2:30][CH3:31])[CH2:27][CH3:28])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8021DiethylamineHCID 24813Phosphorus oxychlorideHCID 21560115HCID 21560115, compound

Product 1

HCID 11807199HCID 11807199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (144 ml, 237 g, 1.55 mol) is added dropwise over a 1.5 hour period to a toluene (800 ml) solution of cyclohexyl-diethylurea (297 g, 1.5 mol). The reaction is stirred overnight at room temperature. Diethylamine (330 ml, 234 g, 3.2 mol) is added dropwise for over a 2 hour period, then stirred 3 hours at room temperature. The reaction mixture is poured into water (3000 ml). The water layer is extracted with toluene (3×200 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-tetraethylguanidine, at 110°-112° C. (334 g, 88%) of 99% purity as judged by gas chromatography. 1H NMR (CD3CN) δ 3.13-3.23 (m, 1H), 3.07 (q, 4H), 2.97 (q, 4H), 1.13-1.77 (m, 10H), 1.0 (t, 6H), 0.98 (t, 6H) ppm.

Workup

  1. stirringstirred 3 hours at room temperature
  2. extractionThe water layer is extracted with toluene (3×200 ml)
  3. dry with materialdried over Na2CO3
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe residue is further distilled under vacuum (ca. 0.3-0.5 torr)
  7. customcollecting product, cyclohexyl-tetraethylguanidine
  8. customat 110°-112° C.

Sources & evidence

ORD record
ord-7d49cedd48844a849f488780183bf5c7
Source dataset
uspto-grants-1997_12
Patent number
US05696290

Reaction notes

Loading…