Phosgene → N-(4-isocyanato-benzyl)-2,2-dimethyl-propionamide

HRID 1057982Notes

Reaction equation

[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][CH:7]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[N:5]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:16])[CH3:14])=[CH:18][CH:19]=1)=[C:1]=[O:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of phosgene (24.1 ml of a 1.93 M solution in toluene, 46.5 mmol) in methylene chloride (50 ml) cooled to 0° C. is added dropwise a solution of N-(4-amino-benzyl)-2,2-dimethyl-propionamide (8 g, 38.8 mmol) and triethyl amine (13.5 ml, 97 mmol) in methylene chloride (80 ml). The reaction mixture is allowed to slowly warm to 25° C. and stirred at this temperature for 18 hrs. The reaction mixture is filtered on dry celite, under an argon atmosphere and the filtrate is concentrated in vacuo. The residue is dissolved in methylene chloride (380 ml) to provide a 0.1 M solution of N-(4-isocyanato-benzyl)-2,2-dimethyl-propionamide in methylene chloride which is used without further purification.

Workup

filtrationThe reaction mixture is filtered
customon dry celite
concentrationunder an argon atmosphere and the filtrate is concentrated in vacuo
dissolutionThe residue is dissolved in methylene chloride (380 ml)

Sources & evidence

ORD record: ord-d73eca34dc454b889a5553ae7d99f52b
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515023B2

Reaction notes

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