Diisopropylethylamine → N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl](2-methoxy)ethoxymethoxyamine

HRID 370373Notes

Reaction equation

HRID 370373 reaction equation
[CH3:1][N:2]([OH:24])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[Cl:20])[CH:6]=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].C(N(C(C)C)CC)(C)C.[CH3:34][O:35][CH2:36][CH2:37][O:38][CH2:39]Br>C(Cl)Cl>[CH3:1][N:2]([O:24][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][C:11]=2[Cl:20])[CH:6]=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 138619491-(Bromomethoxy)-2-methoxyethaneHCID 20275650HCID 20275650, compound

Product 1

HCID 54166899N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl](2-methoxy)ethoxymethoxyamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]hydroxyamine (600 mg, 1.65 mmol) in methylene chloride (4 ml) containing diisopropylethylamine (0.43 ml, 1.5 eq.) is added (2-methoxy)ethoxymethyl bromide (310 mg, 1.5 eq.) The mixture is stirred at RT for 16 hours. The reaction mixture is then taken up in methylene chloride, washed, dried, evaporated and purified by prep. TLC to yield N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl](2-methoxy)ethoxymethoxyamine (IXA, R is CH3OCH2CH2OCH2).

Workup

  1. washwashed
  2. customdried
  3. customevaporated
  4. custompurified by prep

Sources & evidence

ORD record
ord-b9c41369619940319d0e6f2df4ee123f
Source dataset
uspto-grants-1985_07
Patent number
US04526608

Reaction notes

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