Toluene → HCID 20064728, compound

HRID 359261Notes

Reaction equation

HRID 359261 reaction equation
C1(C)C=CC=CC=1.I[C:9]1[O:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1.[CH2:20]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[C:21]1([CH2:20][N:27]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:9]2[O:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7656DibenzylamineHCID 12785853Ethyl 2-iodo-4-methyl-5-oxazolecarboxylate

Product 1

HCID 20064728HCID 20064728, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction vessel fitted with a calcium sulfate drying tube was charged with 5 ml of toluene, 0.56 g (2 mmol) of ethyl 2-iodo-4-methyl-5-oxazolecarboxylate and 2 ml (10 mmol) of dibenzylamine. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then heated at reflux for 4 hours, cooled, and then diluted with ethyl ether. The mixture was washed with water, then with 5% hydrochloric acid, and then with water. The ether solution was dried with sodium sulfate and then concentrated under reduced pressure to yield 0.4 g of a yellow glass. This glass was dissolved in hot hexane and then with the vessel cooling in a dry ice bath, a white solid material was deposited. The solid material was filtered off giving 0.35 g of product (m.p.=75°-77° C.) identified in Table I.

Workup

  1. customA reaction vessel fitted with a calcium sulfate drying tube
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for 4 hours
  4. temperaturecooled
  5. washThe mixture was washed with water
  6. dry with materialThe ether solution was dried with sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-904f9d3177fb489fa6ec43b9aa9b5a15
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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