Benzene → HCID 20256285, compound

HRID 615638Notes

Reaction equation

HRID 615638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][CH2:6][CH2:7][NH:8][CH:9]([CH3:11])[CH3:10].[C:16](Cl)([Cl:18])=[O:17].C1C=CC=CC=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][CH2:6][CH2:7][N:8]([CH:9]([CH3:11])[CH3:10])[C:16]([Cl:18])=[O:17]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6371PhosgeneHCID 88675Proton spongeHCID 20256258HCID 20256258, compound

Product 1

HCID 20256285HCID 20256285, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.53 g (0.018 mole) of 2-(3,5-dichlorophenoxy)-N-(1-methylethyl)ethanamine (oil obtained in Preparation 1), 3.92 g (0.040 moles) phosgene in 21 ml solution of benzene and 3.92 g (0.018 mole) of 1,8-bis(dimethylamino)naphthalene (proton sponge) in 200 ml of methylene chloride was stirred overnight at room temperature. The reaction mixture was extracted with 1N sulfuric acid and the methylene chloride layer thereafter dried over sodium sulfate-sodium carbonate. Evaporation of solvent gave an oil which, when triturated with hexane, gave 1.91 g (34.2%) g of solid. The solid forms a gum on exposure to air which prevents measurement of melting point by conventional means.

Workup

  1. extractionThe reaction mixture was extracted with 1N sulfuric acid
  2. dry with materialthe methylene chloride layer thereafter dried over sodium sulfate-sodium carbonate
  3. customEvaporation of solvent
  4. customgave an oil which, when
  5. customtriturated with hexane
  6. customgave 1.91 g (34.2%) g of solid

Sources & evidence

ORD record
ord-3401f29a00a44e6eb07ab4b8864c7f1b
Source dataset
uspto-grants-1985_02
Patent number
US04500529

Reaction notes

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