Toluene → Allyloxycarbonylaminoacetyl chloride

HRID 1766933Notes

Reaction equation

HRID 1766933 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6])[CH:2]=[CH2:3].CN(C)C=O.C(Cl)(=O)C([Cl:20])=O.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([O:4][C:5]([NH:7][CH2:8][C:9]([Cl:20])=[O:11])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 11964402N-[(allyloxy)carbonyl]glycine

Product 1

HCID 14588174Allyloxycarbonylaminoacetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(allyloxycarbonyl)glycine (described in Chem. Pharm. Bull., 48, 716 (2000); 600 mg, 3.77 mmol) in dichloromethane (15 ml) was cooled to 0° C., and N,N-dimethylformamide (0.03 ml) and oxalyl chloride (0.6 g, 4.7 mmol) were added thereto. The mixture was stirred at room temperature for 1 hour, then toluene was added thereto, and the solvent was distilled off under reduced pressure to give crude 2-(allyloxycarbonylamino)acetyl chloride.

Workup

  1. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a1399b6f79f04d07ba7510fa13d21ea7
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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