Triethylamine → N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-2-nitrobenzamide

HRID 2063201Notes

Reaction equation

HRID 2063201 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH3:17][C:18]1[C:19]([NH2:23])=[N:20][O:21][N:22]=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:17][C:18]1[C:19]([NH:23][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[N:20][O:21][N:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 111923Propylphosphonic anhydrideHCID 184292Benzoic acid, 4-(methylsulfonyl)-2-nitro-

Product 1

HCID 67041744N-(4-methyl-1,2,5-oxadiazol-3-yl)-4-(methylsulfonyl)-2-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

495 mg (2.02 mmol) of 2-nitro-4-methylsulfonylbenzoic acid and 200 mg (2.02 mmol) of 4-methyl-1,2,5-oxadiazol-3-ylamine are dissolved at room temperature (RT) in 5 ml of CH2Cl2 and treated with 0.28 ml (2.02 mmol) of triethylamine, 49 mg (0.40 mmol) of 4-dimethylaminopyridine (DMAP) and 1.93 g (3.03 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 350 mg (53%).

Workup

  1. washsubsequently washed twice with in each case 5 ml of water
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated
  4. customThe residue is purified by column chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-dde437c460174004a98da3b2c8c8b23c
Source dataset
uspto-grants-2012_10
Patent number
US08288316B2

Reaction notes

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