Tetramethylurea → HCID 18952293, compound

HRID 1492198Notes

Reaction equation

HRID 1492198 reaction equation
[CH3:1][N:2]([CH3:8])[C:3](=O)[N:4]([CH3:6])[CH3:5].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.P(Cl)(Cl)(Cl)=O.[IH:27]>C1C=CC=CC=1.CO>[IH:27].[O:19]1[CH2:18][CH2:17][N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:3]([N:4]([CH3:6])[CH3:5])[N:2]([CH3:8])[CH3:1])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 12437TetramethylureaHCID 24813Phosphorus oxychlorideHCID 24841Hydrogen iodideHCID 7357562-Morpholinoaniline

Product 1

HCID 18952293HCID 18952293, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent

Procedure

Reaction of tetramethylurea (10.4 g, 10.7 ml) in dry benzene (80 ml) with 4-(2-aminophenyl)morpholine (10.2 g) in dry benzene (100 ml) in the presence of phosphorus oxychloride (8.3 ml) for 30 hours at 65°-70° C. gave an oil which was purified by column chromotography on a neutral alumina column (100 g) eluted with hexane to give as an oil. A solution of this base (2.5 g) in methanol (10 ml) was treated with 57% hydroiodic acid (1.3 ml) to give 2-(2-morpholinophenyl)-1,1,3,3-tetramethylguanidine hydroiodide as a pale yellow crystalline solid (m.p. 215°-216° C.) which was recrystallised from a 2:3 mixture of methanol and ether.

Workup

  1. customgave an oil which
  2. customwas purified by column chromotography on a neutral alumina column (100 g)
  3. washeluted with hexane
  4. customto give as an oil

Sources & evidence

ORD record
ord-64c6eecc85e74619b05e57d1fddc6a76
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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