Toluene → HCID 53812487, compound

HRID 1939716Notes

Reaction equation

HRID 1939716 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([N:12](CCC)[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:22]([NH:25][CH2:26][CH2:27][CH3:28])[CH2:23][CH3:24].[OH-].[Na+].[C:31]1(C)[CH:36]=CC=C[CH:32]=1>>[CH:6]1([N:12]=[C:13]([N:15]([CH2:16][CH2:17][CH3:18])[CH2:32][CH2:31][CH3:36])[N:25]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:23][CH3:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 5

HCID 1140TolueneHCID 8902DipropylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21468135HCID 21468135, compound

Product 1

HCID 53812487HCID 53812487, compound

Procedure

Phosphorus oxychloride (86 ml, 142 g, 0.92 mol) is added dropwise over a 1 hour period to a toluene (800 ml) solution of cyclohexyl-dipropylurea (191 g, 0.845 mol). The reaction is stirred overnight at room temperature. Dipropylamine (221 g, 300 ml, 2.19) is added dropwise for over a 2 hour period, then stirred 2 hours at room temperature. Sodium hydroxide solution (6×0.92 mol NaOH and 500 ml water) is slowly added to the reaction mixture in an ice-water bath. The water layer is extracted with diethylether (3×100 ml). The organic layers 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-tetrapropylguanidine, at 150° C. (235 g, 90%) of 99% purity as judged by gas chromatography. 1H NMR (CDCl3) δ 3.10 (m, 1H), 3.02 (b , 4H), 2.88 (t, 4H, 1.77-1.12 (m, 10H), 1.42 (q, 8H), 0.82 (t, 6H), 0.80 (t, 6H) ppm.

Workup

  1. stirringstirred 2 hours at room temperature
  2. extractionThe water layer is extracted with diethylether (3×100 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-tetrapropylguanidine
  8. customat 150° C.

Sources & evidence

ORD record
ord-b555c3c3649d43a3a9a9086ad775b52f
Source dataset
uspto-grants-1997_12
Patent number
US05696290

Reaction notes

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