Triethylamine → 6-(4-Isocyanatophenoxy)-hexanoic acid methyl ester

HRID 501840

Reaction equation

HRID 501840 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:26]=[O:28])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester

Product 1

HCID 497644906-(4-Isocyanatophenoxy)-hexanoic acid methyl esterYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To 6-(4-aminophenoxy)-hexanoic acid methyl ester 17 (26 g, 109.7 mmol) and triethylamine (29.2 g, 288.56 mmol) in toluene (390 ml) under nitrogen atmosphere was added triphosgene (15.6 g, 52.56 mmol) in one lot. The reaction was exothermic and internal temperature rose to 60° C. Later the reaction mixture was heated to 75° C. over a period of one hour and maintained at this temperature for 26 hours. The reaction mixture was cooled to room temperature, the solids filtered off, and toluene distilled off under vacuum to get crude 18, which was vacuum distilled to get pure 18 (10 g, 34.7%) with an m.p between 47-50° C.

Workup

  1. customrose to 60° C
  2. temperaturemaintained at this temperature for 26 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe solids filtered off
  5. distillationtoluene distilled off under vacuum
  6. customto get crude 18, which
  7. distillationdistilled

Sources & evidence

ORD record
ord-2d09cca45e6f4f28b69347eb1264a54d
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Linked notes

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