Acetic Acid → Formamide

HRID 1970229Notes

Reaction equation

HRID 1970229 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH:5]([NH2:7])=[O:6].CN([CH:11]=[O:12])C.[CH3:13][C:14](N(C)C)=[O:15]>ClCCCl.C(Cl)Cl>[CH:5]([NH2:7])=[O:6].[C:1]([O:4][C:14](=[O:15])[CH3:13])(=[O:3])[CH3:2].[C:1]([O:4][C:11](=[O:12])[CH2:13][CH3:14])(=[O:3])[CH2:2][CH3:5]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 713FormamideHCID 6228Dimethylformamide2×HCID 31374Dimethylacetamide2×

Product 3

HCID 713FormamideHCID 7918Acetic AnhydrideHCID 31263Propionic anhydride

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

The compounds of formula types A-C may be produced in various ways, for example preferably from the known compounds having general formula types 2, 4 or 8 (see below), in which the letters X and R have the same meaning as above, by heating them with the ammonium salt of a preferably organic acid, such as formic or acetic acid, in a dipolar solvent (Solv) with high boiling point, such as a primary or secondary alkanol having a boiling point above 150° C., an aliphatic carboxylic acid amide, such as formamide, DMF or dimethyl acetamide, or also in a polyvalent alkanol of the 1,2-, 1,3-diol or 1,2,3-triol type, leading to the formation, in a mostly gradual reaction, as described for exemplary purposes by V. F. Donyagina, S. Shimizu, N. Kobayashi and E. A. Lukyanets in Tetrahedron Lett. 2008, 49, 6152, initially of the compounds having general formula type A, recognizable by their deep colours, which are then, following their isolation, reacted as necessary by heating with a compound having general formula ML1L2L3, in which L1 and L2 have the same meaning as above and L3 is a ligand identical to or different from L1 and L2, and like L1 and L2 is able to form a stable coordination sphere with atom M, in a polar solvent, such as a low or higher alkanol, an aliphatic carboxylic acid amide, such as formamide, DMF or dimethyl acetamide, a carboxylic acid anhydride such as acetic acid anhydride or propionic acid anhydride, methylene chloride or 1,2-dichloroethane, to form the target compounds of formula type B or C.

Workup

  1. customreacted as necessary
  2. temperatureby heating with a compound
  3. customto form a stable coordination sphere with atom M

Sources & evidence

ORD record
ord-4240b62e8f1d4de6ad0f78a34f07f7fb
Source dataset
uspto-grants-2013_04
Patent number
US08426850B2

Reaction notes

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