Ethyl isocyanate → 1-[2-Chloro-4-(3-chlorophenoxy)phenoxy]2-ethylaminocarbonyloxyethane

HRID 265622Notes

Reaction equation

HRID 265622 reaction equation
C(N(CC)CC)C.N12CCN(CC1)CC2.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17].[Cl:21][C:22]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)[CH:29]=[CH:28][C:23]=1[O:24][CH2:25][CH2:26][OH:27]>O1CCCC1>[Cl:21][C:22]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)[CH:29]=[CH:28][C:23]=1[O:24][CH2:25][CH2:26][O:27][C:19]([NH:18][CH2:16][CH3:17])=[O:20]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 9237DabcoHCID 190345782-[2-Chloro-4-(3-chlorophenoxy)phenoxy] ethanol

Product 1

HCID 200885701-[2-Chloro-4-(3-chlorophenoxy)phenoxy]2-ethylaminocarbonyloxyethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 ml of triethylamine, 15 mg of 1,4-diazabicyclo[2.2.2]octane and 1.3 g of ethyl isocyanate are added to a solution of 4.49 g of 2-[2-chloro-4-(3-chlorophenoxy)phenoxy] ethanol in 40 ml of tetrahydrofuran. The reaction mixture is heated at 55° for 18 hours, with stirring, and then evaporated to dryness in vacuo. The residue is purified by chromatography [silica gel; diethyl ether/hexane (2:3)]. This gives the title compound which melts at 73°-74° C.

Workup

  1. temperatureThe reaction mixture is heated at 55° for 18 hours
  2. customevaporated to dryness in vacuo
  3. customThe residue is purified by chromatography [silica gel; diethyl ether/hexane (2:3)]

Sources & evidence

ORD record
ord-4fbe3223653146fa8f3244ea0afe1d5c
Source dataset
uspto-grants-1997_07
Patent number
US05648494

Reaction notes

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