Triethylamine → HCID 58894692, compound

HRID 1676849Notes

Reaction equation

HRID 1676849 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=[O:4].C(N(CC)CC)C.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([N:14]=[C:24]=[O:26])=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 58566935HCID 58566935, compound

Product 1

HCID 58894692HCID 58894692, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 4-amino-benzoic acid methoxycarbonylmethyl ester 6 (10 grams, 47.84 mmol) and triethylamine (9.68 grams, 95.67 mmol) in toluene (150 mL) under nitrogen atmosphere at 0° C. is added triphosgene (5.195 grams, 17.50 mmol) in one lot. Later the reaction mixture is heated to 75° C. over a period of one hour and maintained at this temperature for 20 hours. The reaction mixture is cooled to room temperature. The solids are filtered off, and the toluene is distilled under vacuum to give crude 11, which can be purified by a suitable method.

Workup

  1. temperaturemaintained at this temperature for 20 hours
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationThe solids are filtered off
  4. distillationthe toluene is distilled under vacuum
  5. customto give crude 11, which
  6. customcan be purified by a suitable method

Sources & evidence

ORD record
ord-48d864cf492b4601b4929f92a9d428af
Source dataset
uspto-grants-2011_08
Patent number
US08007526B2

Reaction notes

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