N,N'-Dicyclohexylurea → 1-(2-Methylthiazole-5-carbonyl)-2-cyanoaziridine

HRID 2286577Notes

Reaction equation

HRID 2286577 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.[C:10]([CH:12]1[CH2:14][NH:13]1)#[N:11].C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O>C(OCC)C.O1CCCC1>[CH3:1][C:2]1[S:3][C:4]([C:7]([N:13]2[CH2:14][CH:12]2[C:10]#[N:11])=[O:9])=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 988455-Thiazolecarboxylic acid, 2-methyl-HCID 118115Aziridine-2-carbonitrile

Product 1

HCID 234614801-(2-Methylthiazole-5-carbonyl)-2-cyanoaziridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.6 g. 2-Methylthiazole-5-carboxylic acid (m.p. 209° C.) and 0.76 g. 2-cyanoaziridine in 20 ml. tetrahydrofuran are mixed at 0° to 5° C. with 2.4 g. dicyclohexylcarbodiimide. The reaction mixture is stirred for 1 hour at 0° C. and for 3 hours at ambient temperature, whereafter the precipitated dicyclohexylurea is filtered off with suction and washed with the above-mentioned solvent and with diethyl ether. The filtrate is evaporated in a vacuum and the evaporation residue is taken up in ethyl acetate and shaken out with a saturated aqueous solution of sodium bicarbonate. The organic phase is dried and evaporated in a vacuum to give 2.38 g. of an oil. This oily residue is dissolved in 90 ml. diethyl ether, left to stand overnight, precipitated dicyclohexylurea is filtered off with suction, the ethereal solution is evaporated and the evaporation residue is triturated with a little diethyl ether, 1.4 g. 1-(2-methylthiazole-5-carbonyl)-2-cyanoaziridine being obtained; m.p. 90°- 92° C.

Workup

  1. filtrationis filtered off with suction
  2. washwashed with the above-mentioned solvent and with diethyl ether
  3. customThe filtrate is evaporated in a vacuum
  4. customThe organic phase is dried
  5. customevaporated in a vacuum
  6. customto give 2.38 g
  7. dissolutionThis oily residue is dissolved in 90 ml
  8. customprecipitated dicyclohexylurea
  9. filtrationis filtered off with suction
  10. customthe ethereal solution is evaporated
  11. customthe evaporation residue is triturated with a little diethyl ether, 1.4 g

Sources & evidence

ORD record
ord-a6fa6f7696d745fa816b1a9886377e89
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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