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

HRID 638725

Reaction equation

HRID 638725 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 a mixture of 6-(4-amino-phenoxy) hexanoic acid methyl ester 21 (26 grams, 109.7 mmol) and triethylamine (29.2 g, 288.56 mmol) in toluene (390 ml) under nitrogen atm. was added triphosgene (15.6 grams, 52.56 mmol) in one lot. The reaction was exothermic and the 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 were filtered, and the toluene was distilled off under vacuum to get crude 36, which was vacuum distilled to get pure 36 (10 g, 34.7%). M.p: 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 were filtered
  5. distillationthe toluene was distilled off under vacuum
  6. customto get crude 36, which
  7. distillationdistilled

Sources & evidence

ORD record
ord-cf37ab8dbac84da9a6c6b8284979948b
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Linked notes

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