Sodium Azide → 4-Acetylamino-5-chloro-2-methoxy-benzoyl azide

HRID 27716

Reaction equation

HRID 27716 reaction equation
[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9](Cl)=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+]>CC(C)=O>[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([N:17]=[N+:18]=[N-:19])=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 113799924-Acetamido-5-chloro-2-methoxybenzoyl chloride

Product 1

HCID 205387424-Acetylamino-5-chloro-2-methoxy-benzoyl azideYield 209.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution of 4-acetylamino-5-chloro-2-methoxy-benzoyl chloride (e6) (2.0 g) was added to a stirred aqueous solution of sodium azide (2.0 g) and the suspension stirred at room temperature for 30 minutes. Extraction with ethyl acetate gave 4-acetylamino-5-chloro-2-methoxy-benzoyl azide (e7) (4.3 g) as a white crystalline solid on trituration under petrol, m.p. 135°-140°. [I.R.ν(N3)=2140 cm-1 and ν(C=O)=1645, 1705 cm-1 ]

Workup

  1. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-98c38c2bcee94924b3fb7a328652a258
Source dataset
uspto-grants-1980_09
Patent number
US04223034

Linked notes

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