Iodoacetamide → HCID 19697618, compound

HRID 863253Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([OH:11])[CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][C:23]([NH2:25])=[O:24]>>[C:23]([CH2:22][O:11][C:9]1[CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[CH:7][C:8]=1[N+:12]([O-:14])=[O:13])(=[O:24])[NH2:25]

Participants

Reactant 3

HCID 3727Iodoacetamide

HCID 11430Potassium Carbonate

HCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 19697618HCID 19697618, compound

Procedure

Reaction of 1.08 g of 5-methoxycarbonyl-2-nitrophenol, 1.82 g of potassium carbonate and 2.02 g of iodoacetamide gives 2-carbamoylmethoxy-4-(methoxycarbonyl)nitrobenzene of mp 138°-9° C.; Rf (O)=0.63; FAB-MS: (M+H)+ 255; anal. calc. for C10H10N2O6 : C47.25%, H3.97%, N11.02%; found C47.08%, H4.04%, N10.79%. Starting from 1.16 g of 2-carbamoylmethoxy-4-(methoxycarbonyl)nitrobenzene, 2-carbamoylmethoxy-4-(methoxycarbonyl)aniline of mp 178°-80° C.; Rf (O)=0.37; MS: M+ =224; anal, calc. for C10H12 N2O4 : C53.57%, H5.39%, N12.49%; found C53.41%. H5.32%, N12.53%.

Sources & evidence

ORD record: ord-4819cfc409b34ff7a9a0f7ee32948f19
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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