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

HRID 2185958Notes

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 cellite, 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 as is.

Workup

filtrationThe reaction mixture is filtered
customon dry cellite
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-c1924ccd5cc8485197e0d694034c6700
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403612B2

Reaction notes

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