Sodium Hydroxide → Clazolimine

HRID 2420362Notes

Reaction equation

HRID 2420362 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]#[N:12])=[CH:6][CH:5]=1.[CH3:13][NH:14][C:15](=O)[CH2:16]Cl>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:16][C:15](=[O:1])[N:14]([CH3:13])[C:11]2=[NH:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 667732-chloro-N-methylacetamideHCID 2735790Cyanamide, (4-chlorophenyl)-

Product 1

HCID 38683Clazolimine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 25 ml. of water containing 0.84 g. of sodium hydroxide was dissolved in 3.2 g. of p-chlorophenylcyanamide. To the clear solution was added 2.25 g. of N-methylchloroacetamide. The reaction mixture was stirred for 48 hours at room temperature. The precipitate was filtered to yield 1.9 g. of product, m.p. 182°-184° C. After the initial product was filtered, the filtrate was left stirring another three days. An additional 1.2 g. of product precipitated from solution. Total yield of product was 3.1 g. (66%).

Workup

  1. additionTo the clear solution was added 2.25 g
  2. filtrationThe precipitate was filtered
  3. customto yield 1.9 g
  4. filtrationAfter the initial product was filtered
  5. waitthe filtrate was left
  6. stirringstirring another three days
  7. customof product precipitated from solution

Sources & evidence

ORD record
ord-5fa5e1d65f7c4b00bf98fc3955064a78
Source dataset
uspto-grants-1978_08
Patent number
US04110445

Reaction notes

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