Benzene → HCID 20275654, compound

HRID 370372Notes

Reaction equation

HRID 370372 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].N1C=CC=CC=1.C1C=CC=CC=1.[Cl:37][C:38]([Cl:43])([CH3:42])[C:39](Cl)=[O:40]>C(Cl)Cl>[CH3:1][N:2]([O:24][C:39](=[O:40])[C:38]([Cl:43])([Cl:37])[CH3:42])[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

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 943632,2-Dichloropropanoyl chlorideHCID 20275650HCID 20275650, compound

Product 1

HCID 20275654HCID 20275654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]hydroxyamine (500 mg, 1.38 mmol) in methylene chloride (2 ml) is added pyridine (0.16 ml, 2.00 mmol) and benzene (3 ml), followed by α,α-dichloropropionyl chloride (328 mg, 1.5 eq.). The mixture is stirred at RT for 2 hours. The resulting reaction mixture is then taken up in methylene chloride, washed, dried and evaporated to dryness. The crude product is purified by prep. TLC to yield N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-α,α-dichloropropionyloxyamine. nmr (CDCl3) τ7.77(S,3H,COC Cl2CH3), 6.67(S, 3H, NCH3).

Workup

  1. customThe resulting reaction mixture
  2. washwashed
  3. customdried
  4. customevaporated to dryness
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-37d93978a8214f04b5dea709ee63d2f0
Source dataset
uspto-grants-1985_07
Patent number
US04526608

Reaction notes

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