Dimethylformamide → HCID 18348749, compound

HRID 2268017Notes

Reaction equation

HRID 2268017 reaction equation
C(Cl)(=O)C(Cl)=O.Cl.[N:8]1[S:9][C:10](=[N:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12.CN(C)C=O.CNO>ClCCl.C(N(CC)CC)C.O.O1CCCC1>[N:8]1[S:9][C:10](=[N:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 11647MethylhydroxylamineHCID 65578Oxalyl chlorideHCID 69926500HCID 69926500, compound

Product 1

HCID 18348749HCID 18348749, compoundYield 79.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 1.7 ml of oxalyl chloride in 15 ml of dichloromethane is added dropwise at 0° C. to a mixture of 4.8 g (15 mmol) of the compound of Example 8, 90 ml of dichloromethane and 1 ml of dimethylformamide. The solution obtained is stirred for 40 min and then added dropwise to a solution of 5.0 g of N-methylhydroxylamine in 15 ml of triethylamine, 10 ml of water and 60 ml of tetrahydrofuran. After stirring for 30 min, the mixture is treated with 20 ml of water and extracted with dichloromethane, the extract is dried and concentrated, and the residue is purified on silica gel (eluent trichloroethane/methanol 95:5). 3.4 g of title compound (78% of theory) are isolated, which after trituration with ether melt at 135-136° C.

Workup

  1. customThe solution obtained
  2. stirringAfter stirring for 30 min
  3. extractionextracted with dichloromethane
  4. customthe extract is dried
  5. concentrationconcentrated
  6. customthe residue is purified on silica gel (eluent trichloroethane/methanol 95:5)

Sources & evidence

ORD record
ord-bbea42a4397f4abab1f84cdeeda27d3f
Source dataset
uspto-grants-2001_12
Patent number
US06326378B1

Reaction notes

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