Acetoxyacetyl chloride → 5-Acetoxyacetamido-3-methylcarbamoyl2,4,6-triiodobenzoyl chloride

HRID 1707903Notes

Reaction equation

[NH2:1][C:2]1[C:3]([I:17])=[C:4]([C:13](=[O:16])[NH:14][CH3:15])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19]>CN(C)C(=O)C.CN(C)C1C=CN=CC=1>[C:18]([O:21][CH2:22][C:23]([NH:1][C:2]1[C:3]([I:17])=[C:4]([C:13](=[O:16])[NH:14][CH3:15])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8])=[O:24])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of (2) (170 g, 0.29 mol) in 350 ml of N,N-dimethylacetamide (DMAc) was added 4-dimethylaminopyridine (DMAP) (1.86 g, 0.015 mol). The mixture was cooled to 0° C. and acetoxyacetyl chloride (62 ml, 78.6 g, 0.58 mol) was added dropwise, keeping the temperature <5° C. The mixture was stirred at 30° C. for 16 hours. The reaction mixture containing the solid white product was immersed in an ice bath for 2 hours, filtered, stirred with cold THF (1100 ml) for 1 hour, filtered and dried under vacuum for 2 days to give 190 g of product 3 (0.30 mol, 95%) as a white solid. 13C NMR (75.5 MHz, DMSO, ref. DMSO at 39.5 ppm): 170.6, 170.2, 169.9, 166.1, 166.0, 151.7, 149.8, 143.6, 143.5, 103.4, 97.0, 88.8, 62.4, 26.0, 20.6.

Workup

customthe temperature <5° C
additionThe reaction mixture containing the solid white product
waitwas immersed in an ice bath for 2 hours
filtrationfiltered
stirringstirred with cold THF (1100 ml) for 1 hour
filtrationfiltered
customdried under vacuum for 2 days

Sources & evidence

ORD record: ord-41a1e7b22cd9497fb7724edc1c8e3f0c
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356613

Reaction notes

Loading…