Formic Acid → HCID 44330132, compound

HRID 1788368Notes

Reaction equation

HRID 1788368 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH2:33][CH:34]([NH:42][OH:43])[CH:35]=[C:36]3[CH2:41][CH2:40][S:39][CH2:38][CH2:37]3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>O1CCCC1>[OH:43][N:42]([CH:34]([CH:35]=[C:36]1[CH2:37][CH2:38][S:39][CH2:40][CH2:41]1)[CH2:33][S:30]([C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:11])[CH:21]=2)=[CH:29][CH:28]=1)(=[O:31])=[O:32])[CH:1]=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86595271HCID 86595271, compound

Product 1

HCID 44330132HCID 44330132, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of formic acid (3.0 mL) and acetic anhydride (0.4 mL) premixed for 30 minutes at 0° C. was added to a solution of 0.28 g (0.58 mmol) of N-{2-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-1-(tetrahydrothiopyran-4-ylidenemethyl)ethyl}hydroxylamine (III-17) in tetrahydrofuran (4 mL) at 0° C., and stirred for another 2 hours at room temperature. After the reaction was completed, the solvent was removed under a reduced pressure, and then subjected to azeotropic distillation with toluene. The resulting residue was dissolved in a mixed solution of methanol (1 mL) and chloroform (3 mL) and stirred for 1 hour at room temperature. Then, the solvent was removed under a reduced pressure, and the obtained residue was subjected to medium pressure column chromatography on silica gel (developing solvent; chloroform:methanol=30: 1) to obtain 0.1 g (yield 34%) of the title compound as a white crystal. Its physical properties are shown below.

Workup

  1. additionpremixed for 30 minutes at 0° C.
  2. customthe solvent was removed under a reduced pressure
  3. distillationsubjected to azeotropic distillation with toluene
  4. dissolutionThe resulting residue was dissolved in a mixed solution of methanol (1 mL) and chloroform (3 mL)
  5. stirringstirred for 1 hour at room temperature
  6. customThen, the solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-18b3ab9748cd4cdf92b31b488066b298
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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