Ethyl 2-(2-bromoacetyl)benzoate → ethyl 2-(N,N-diformylglycyl)benzoate

HRID 1870804Notes

Reaction equation

C(N(C=O)CC(C1C=CC=CC=1C#N)=O)=O.[CH:17]([N-:19][CH:20]=[O:21])=[O:18].[Na+].Br[CH2:24][C:25]([C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:26]>C(#N)C>[CH:17]([N:19]([CH:20]=[O:21])[CH2:24][C:25]([C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:26])=[O:18]

Participants

Conditions

Temperature: 20 °C

Procedure

The 2-(N,N-diformylglycyl)benzonitrile can be prepared in the following manner: 5.54 g of sodium diformylamide are added to a solution of 14.45 g of ethyl 2-bromoacetylbenzoate in 150 ml of acetonitrile and the mixture is stirred for 16 hours at boiling temperature and then, after cooling to 20° C., the insoluble matter produced is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C. The residue is chromatographed on a neutral silica gel, eluting with a methylene chloride-ethyl acetate (80-20 by volume) mixture. 8.4 g of ethyl 2-(N,N-diformylglycyl)benzoate are thus obtained in the form of an orange-coloured oil [1H spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 1.22 (3H, t, J=6 Hz, CH3), 4.23 (2H, q, J=6 Hz, OCH2), 4.90 (2H, s, NCH2CO), between 7.60 and 7.90 (4H, m, 4 arom. CH), 9.20 (2H, s, 2 CHO)].

Workup

customthe insoluble matter produced
customis removed by filtration
concentrationthe filtrate is concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C
customThe residue is chromatographed on a neutral silica gel
washeluting with a methylene chloride-ethyl acetate (80-20 by volume) mixture

Sources & evidence

ORD record: ord-1db040a821c947559af4b3daa7f90d2d
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100264

Reaction notes

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