4-Toluenesulfonyl chloride → Dicyclohexylcarbodiimide

HRID 1264155Notes

Reaction equation

HRID 1264155 reaction equation
[CH:1]1([NH:7][C:8]([NH2:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([C:14]1[CH:20]=[CH:19][C:17](C)=[CH:16][CH:15]=1)(=O)=O>>[CH2:4]1[CH2:5][CH2:6][CH:1]([N:7]=[C:8]=[N:10][CH:14]2[CH2:20][CH2:19][CH2:17][CH2:16][CH2:15]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69684Cyclohexylurea

Product 1

HCID 10868Dicyclohexylcarbodiimide

Procedure

The polymer bound cyclohexylurea (PS-DCU; 1 g of 1.25 mmol/g) recovered after N-acylation is suspended in dimethylformamide (DMF; 10 ml) in a two-necked round-bottom flask (50 ml) equipped with a silicone rubber septum and a reverse filter funnel under exclusion of moisture and air. Tosyl chloride (TsCl; 0.47 g, 2.5 mmol) is added slowly over a period of 20 minutes to the above suspension of PS-DCU. The mixture is shaken gently for 8-10 hours and supernatant is removed by reverse filtration and replaced by 10% aqueous NaOH (5 ml) and tetrahydrofuran (20 ml). The suspension is shaken for 1 hour and supernatant is removed. The polymer is washed with tetrahydrofuran (2×25 ml) to remove excess of water, DMF and base and dried under vacuum to furnish PS-DCC.

Workup

  1. customrecovered after N-acylation
  2. customis suspended in dimethylformamide (DMF; 10 ml) in a two-necked round-bottom flask
  3. custom(50 ml) equipped with a silicone rubber septum
  4. filtrationa reverse filter funnel under exclusion of moisture and air
  5. customsupernatant is removed by reverse filtration
  6. stirringThe suspension is shaken for 1 hour
  7. customsupernatant is removed
  8. washThe polymer is washed with tetrahydrofuran (2×25 ml)
  9. customto remove excess of water, DMF and base
  10. customdried under vacuum

Sources & evidence

ORD record
ord-95ede9ca052445a7b65846336b6f5c1d
Source dataset
uspto-grants-2003_04
Patent number
US06541626B2

Reaction notes

Loading…