Diethyl Ether → HCID 19736594, compound

HRID 326279Notes

Reaction equation

HRID 326279 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:7][C:8](=[O:17])[C:9]1[C:10](=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[NH2:11])[CH3:6].C(N(CC)CC)C.CCOCC>C1(C)C=CC=CC=1.O1CCCC1>[CH2:5]([O:7][C:8]([C:9]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]=1[N:11]=[C:1]=[O:2])=[O:17])[CH3:6]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6371PhosgeneHCID 8471TriethylamineHCID 12327279Ethyl 2-amino-4-chlorobenzoate

Product 1

HCID 19736594HCID 19736594, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of phosgene in toluene (36.3 ml×20%) was added dropwise over 30 min to a stirred solution of ethyl-4-chloroanthranilate (10.0 g) and triethylamine (15 ml) in dry tetrahydrofuran at -5° C. The temperature was maintained at -5° C. for 1 h and then allowed to warm to room temperature. After 1 h ether (200 ml) was added and the solution filtered. Removal of solvent under reduced pressure afforded the product as a white solid (11.2 g). δ(CDCl3) 1.39 (3H, t, J=7.5 Hz, CH2CH3), 4.34 (2H, q, J=7.5 Hz, CH2CH3), 7.22 (1H, d, J=CH2CH3, 1.0 Hz, H-6), 7.28 (1H, dd, J=6.5 and 1.0 Hz, H-4), 8.31 (1H, d, J=6.5 Hz, H-3); m/z (EI +) 225.

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe solution filtered
  3. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-ec880d5ade304b07875a7f86ea52ee76
Source dataset
uspto-grants-1993_12
Patent number
US05268378

Reaction notes

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