Triethylamine → HCID 22119968, compound

HRID 1274641Notes

Reaction equation

HRID 1274641 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([OH:23])=O)[C:17]=3[CH:24]=2)[C:3]1=[O:25].C(Cl)(=O)C(Cl)=O.Cl.[CH3:33][O:34][NH2:35].C(N(CC)CC)C>CN(C)C=O.O1CCCC1.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([NH:35][O:34][CH3:33])=[O:23])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 111878605-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid

Product 1

HCID 22119968HCID 22119968, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid (4.00 g, 0.0108 mol), methylene chloride and tetrahydrofuran on an ice bath is added N,N-dimethylformamide (5 drops) followed by oxalyl chloride (13.5 ml, 0.0269 mol). The resultant mixture is stirred 90 minutes at ambient temperature and concentrated in vacuo. The residue is taken up in tetrahydrofuran and 25% of the solution is added to a mixture of O-methyl hydroxylamine hydrochloride (0.900 g, 0.0108 mol), tetrahydrofuran and triethylamine (2.25 ml, 0.0162 mol). The resultant mixture is stirred overnight at room temperature, poured into ice water, and extracted with methylene chloride. The organic layers are dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel with methylene chloride to give the title compound as a light yellow solid (0.240 g, 22.3%, mp 125-127° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layers are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-f5af579a26fc4e6da1a476c3143818cd
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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