Diazomethane → HCID 53649795, compound

HRID 617006Notes

Reaction equation

HRID 617006 reaction equation
[N+:1](=[CH2:3])=[N-:2].[CH:4]([C:12](Cl)=[O:13])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOCC.C(Cl)Cl>[N+:1](=[CH:3][C:12]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:13])=[N-:2]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 53649795HCID 53649795, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diazomethane (9.66g, 0.23 mole) in dry ether (1250 ml.) maintained at 0° to -5°, was added a suspension of the styrene-carbonyl chloride polymer (10.0g) from example 7(c) in methylene chloride (50 ml.) over 15 minutes. Stirring was maintained for 5 hours at 0° to -5° and then for 16 hours at room temperature. The reaction mixture was filtered and the polymer washed with ether (2 × 100 ml.) and chloroform (2 × 100 ml.) and dried in vacuo at room temperature to constant weight. The title polymer (10.76g) was deep yellow in colour and the IR spectrum exhibited absorptions at 2100 (diazo) and 1610 (carbonyl) cm-1. The composition of the polymer was confirmed by microanalysis.

Workup

  1. additionwas added
  2. temperaturewas maintained for 5 hours at 0° to -5°
  3. filtrationThe reaction mixture was filtered
  4. washthe polymer washed with ether (2 × 100 ml.) and chloroform (2 × 100 ml.)
  5. customdried in vacuo at room temperature to constant weight

Sources & evidence

ORD record
ord-3da29e58ce754d26ace2d50a8288c8af
Source dataset
uspto-grants-1978_02
Patent number
US04076913

Reaction notes

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