Diisopropylethylamine → HCID 22286309, compound

HRID 2218461Notes

Reaction equation

HRID 2218461 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[CH:14][C:10]=2[C:11]([OH:13])=O)=[C:4]([CH3:21])[CH:3]=1.[CH:22]([O:24][CH2:25][CH2:26][O:27][NH2:28])=[CH2:23].C(N(C(C)C)CC)(C)C.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F>ClCCl.CCOCC>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[CH:14][C:10]=2[C:11]([NH:28][O:27][CH2:26][CH2:25][O:24][CH:22]=[CH2:23])=[O:13])=[C:4]([CH3:21])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 98876302-(4-iodo-2-methylphenylamino)-3,4,5-trifluorobenzoic acidHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamine

Product 1

HCID 22286309HCID 22286309, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution comprised of 2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-benzoic acid (3.60 g, 8.84 mmol), O-(2-vinyloxyethyl)hydroxylamine (1.09 g, 10.5 mol) and diisopropylethylamine (2.80 mL, 16.0 mmol) in dichloromethane (50 mL) was added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium-hexafluorophosphate (5.26 g, 10.1 mmol). The resultant solution was stirred 90 min at ambient temperature. The reaction mixture was diluted with ether (100 mL) and washed with water (3×50 mL) and saturated brine (50 mL). The organics were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography to afford 2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-N-(2-vinyloxyethoxy)benzamide (3.17 g, 73%) as a pale-yellow foam.

Workup

  1. washwashed with water (3×50 mL) and saturated brine (50 mL)
  2. dry with materialThe organics were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-38c9df97c5a248fb99f4c0b9d06a1168
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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