Triethylamine → (6-Hydroxy-hexyl)carbamic acid 4-phenoxy-phenyl ester

HRID 260335Notes

Reaction equation

HRID 260335 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:26])OC2C=CC([N+]([O-])=O)=CC=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].C(N(CC)CC)C>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15](=[O:26])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199606-Amino-1-hexanolHCID 54343370Carbonic Acid (4-nitrophenyl)ester (4-phenoxy-phenyl)ester

Product 1

HCID 53701573(6-Hydroxy-hexyl)carbamic acid 4-phenoxy-phenyl esterYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the carbonate prepared in Example 1 (10.0 g, 28.4 mmol) in 75 mL of methylene chloride was added under nitrogen dropwise to a solution of 6-amino-1-hexanol (3.34 g, 28.4 mmol) and triethylamine (19.8 mL, 142 mmol) in 100 mL of methylene chloride at ice-bath temperature. The reaction was stirred at ice bath temperature for approximately eight hours and at room temperature overnight. The reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 8.1 g of a solid. Recrystallization of the solid from diisopropyl ether gave 6.55 g (70%) of the title compound as a white crystalline solid, mp 72°-75° C.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-06486d071e464a83afeca12d65d77088
Source dataset
uspto-grants-1996_06
Patent number
US05527804

Reaction notes

Loading…