Methanol → HCID 10282540, compound

HRID 1821084Notes

Reaction equation

HRID 1821084 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:8][CH2:9][NH:10][CH2:11][C:12](=[CH2:27])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:34][OH:35].[N-:36]=[C:37]=O.Cl[CH2:40][Cl:41]>>[Cl:41][C:40]1[CH:5]=[CH:6][CH:1]=[CH:2][C:3]=1[CH2:37][NH:36][C:34]([N:10]([CH2:11][C:12](=[CH2:27])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:35]

Participants

5

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 105034Isocyanate3×HCID 11374331HCID 11374331, compound

Product 1

HCID 10282540HCID 10282540, compoundYield 90%

Procedure

The secondary amine (7) obtained in Stage 2 of Example 24 (145 mg, 1 eq, 0.32 mmol) is introduced in solution in dichloromethane (10 mL) into tubes (10). Then the corresponding isocyanate (from 1.09 to 1.17 eq) is added to each tube. The reaction media are stirred for 2 hours at ambient temperature. The PS-Tisamine (reagent supported on resin) (3 eq/excess of isocyanate) is then introduced into each of the tubes, and the reaction media are stirred again for 45 minutes at ambient temperature. This operation is carried out again if any isocyanate remains. The resin is then eliminated by filtration, and the solvent is driven off using a centrifuge under vacuum (speedvac), in order to finally recover the desired product originating from the condensation carried out. In this way the desired urea is obtained with a yield of approximately 90%.

Workup

  1. customThe reaction media
  2. customthe reaction media
  3. stirringare stirred again for 45 minutes at ambient temperature
  4. filtrationThe resin is then eliminated by filtration
  5. customin order to finally recover the desired product originating from the condensation

Sources & evidence

ORD record
ord-f0e363ca29d440cb8899d76da7a62c6f
Source dataset
uspto-grants-2009_10
Patent number
US07605261B2

Reaction notes

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