Dimethylformamide → HCID 58474813, compound

HRID 1400870Notes

Reaction equation

HRID 1400870 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:22])[C:16]([C:19](O)=[O:20])=[CH:17][N:18]=3)[S:13][C:6]=12.CN(C=O)C.C(Cl)(=O)C([Cl:38])=O>C1COCC1>[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:22])[C:16]([C:19]([Cl:38])=[O:20])=[CH:17][N:18]=3)[S:13][C:6]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58207740HCID 58207740, compound

Product 1

HCID 58474813HCID 58474813, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a pre-cooled solution of acid 214 (1.25 g, 3.02 mmol, scheme 52) in THF (12.07 mL) was added DMF (0.023 mL, 0.302 mmol) and oxalyl chloride (0.660 mL, 7.54 mmol) and the resultant solution was stirred at 0° C. for 30 min. The solvent was evaporated, the residue was triturated with ether and dried under high vacuum to give title compound 219 (1.306 g, 3.02 mmol, 100% yield) as a beige solid. MS: 429.2 (MH+, COOMe), 433.1 (COCl, MH+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with ether
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-45452f89ad404ccaaa07084b2f82fa53
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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