Phenol → N,N'-Dicyclohexylurea

HRID 848631Notes

Reaction equation

HRID 848631 reaction equation
C1([OH:7])C=CC=CC=1.[CH:8]1([N:14]=[C:15]=[N:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N1C2C(=CC=CC=2)C(CCCC(O)=O)=C1>O1CCCC1>[C:15]([NH:14][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:7]

Participants

5

Reactant 3

HCID 996Phenol2×HCID 8617Indole-3-Butyric Acid2×HCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-DicyclohexylureaYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Phenol (0.46 g., 0.005 mole), dicyclohexylcarbodiimide (1.01 g, 0.005 mole) and indole-3-butyric acid (1.00 gm. 0.005 mole) were dissolved in minimal amounts of tetrahydrofuran in individual glass-stoppered Erlenmeyer flasks. Indole-3-butyric acid and dicyclohexylcarbodiimde solutions were mixed together and allowed to react for 15 minutes. The phenol solution was then added and the mixture allowed to react for 48 hours at room temperature. The mixture was then cooled in a refrigerator (0° C.). Dicyclohexylurea crystals which formed were filtered, washed with cold tetrahydrofuran, and the filtrate reduced in volume. Filtration, washing, and volume reduction were repeated four times.

Workup

  1. customto react for 15 minutes
  2. customto react for 48 hours at room temperature

Sources & evidence

ORD record
ord-0d1a3462983c4bd99ab2d0a56e2b9fe0
Source dataset
uspto-grants-1981_10
Patent number
US04297125

Reaction notes

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