Oxalyl chloride → HCID 12905148, compound

HRID 1155285Notes

Reaction equation

HRID 1155285 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[C:7]([O:10][C:11]1[C:19]([O:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=[O:14])(=[O:9])[CH3:8]>ClCCCl>[C:7]([O:10][C:11]1[C:19]([O:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([N:15]=[C:2]=[O:3])=[O:14])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 12336141HCID 12336141, compound

Product 1

HCID 12905148HCID 12905148, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Oxalyl chloride (5.3 g) was added to a solution of 2,3-diacetoxybenzamide (4.0 g) in 1,2-dichloroethane (40 ml) while stirring under cooling. The mixture was gradually heated to a reflux temperature and allowed to react under reflux for 10 hours. Then, the solvent and excess oxalyl chloride were distilled off under reduced pressure to give 2,3-diacetoxybenzoyl isocyanate, which was dissolved in dried dichloromethane (40 ml) for the subsequent reaction. (2) N,O-Bis(trimethylsilyl)acetamide (19 ml) was added dropwise at room temperature to a suspension of D(-)-phenylglycine (5.3 g) in dried dichloromethane (100 ml) at room temperature followed by stirring until the mixture was made uniform. The solution previously obtained in (1) above was added dropwise to the clear solution at a temperature of from 5° to 10° C. After stirring the mixture for 1.5 hours at the same temperature, the mixture was evaporated to dryness at room temperature under reduced pressure. To the residue was added dried methanol and evaporated to dryness under reduced pressure. To the residue was added cold diluted aqueous hydrochloric acid (200 ml) and the mixture was stirred for 5 to 10 minutes. The resulting white precipitates were collected by filtration and dissolved in a cold, saturated sodium bicarbonate aqueous solution (250 ml), and the insoluble sobstances were removed by filtration. The filtrate was washed with ethyl acetate (250 ml) and, after adjusting its pH to about 1 with cold 2 N hydrochloric acid, the resulting white precipitates were collected by filtration, washed with water and then diethyl ether, and dried in air to give 4.5 g of D(-)-α-[3-(2,3-diacetoxybenzoyl)-1-ureido]phenylacetic acid as a white powder. m.p. 200°-201° C. (decomposition).

Workup

  1. temperatureunder cooling
  2. temperatureThe mixture was gradually heated to a reflux temperature
  3. customto react
  4. temperatureunder reflux for 10 hours
  5. distillationThen, the solvent and excess oxalyl chloride were distilled off under reduced pressure

Sources & evidence

ORD record
ord-1234207f510b430a8790409489ce073b
Source dataset
uspto-grants-1981_11
Patent number
US04301161

Reaction notes

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