Dicyclohexylcarbodiimide → HCID 20029866, compound

HRID 1721903Notes

Reaction equation

HRID 1721903 reaction equation
[CH2:1]1[CH2:6]CC(N=C=NC2CCCCC2)C[CH2:2]1.[I:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(O)CC>[I:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([O:23][CH2:2][CH2:1][CH3:6])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 120854-Iodobenzoic acid

Product 1

HCID 20029866HCID 20029866, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 10311-PropanolSolvent

Procedure

DCC (13.4 g) was added in one portion to 4-iodobenzoic acid (15.0 g), n-propanol (7.2 g) and 4-(dimethylamino)pyridine (0.6 g) in MC (50 ml) at 0° under nitrogen. The mixture was stirred at 0° for 10 min and at room temperature for 3 h, diluted with ER (50 ml), filtered and evaporated. The residue was treated with CX (50 ml), filtered and the filtrate evaporated to give the title compound as a pale yellow oil (16.2 g). T.l.c. (CX-ER 3:1) Rf 0.8.

Workup

  1. additiondiluted with ER (50 ml)
  2. filtrationfiltered
  3. customevaporated
  4. additionThe residue was treated with CX (50 ml)
  5. filtrationfiltered
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-2518056eb67c4ea184b63cc968363b91
Source dataset
uspto-grants-1989_08
Patent number
US04853382

Reaction notes

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