4-Methylmorpholine → HCID 178521406, compound

HRID 1681669Notes

Reaction equation

HRID 1681669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](O)=[O:21])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:40][C:41]1[NH:45][N:44]=[N:43][N:42]=1>CN(C)C=O.C(Cl)Cl>[NH:42]1[C:41]([NH:40][C:20](=[O:21])[CH2:19][O:18][C:17]2[CH:23]=[CH:24][C:14]([CH2:13][CH2:12][NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[CH:15][CH:16]=2)=[N:45][N:44]=[N:43]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 15103333HCID 15103333, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178521406HCID 178521406, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a suspension of 7.30 g. (20 mMol) 4-[2-(4-chlorobenzenesulphonamido)-ethyl]-phenoxyacetic acid (preparation see European Patent Specification No. 0,239,907) and 2.20 ml. 4-methylmorpholine in 60 ml. dry methylene chloride is added dropwise at -10° C. 2.76 g. (20 mMol) isobutyl chloroformate, dissolved in 40 ml. dry methylene chloride, within the course of 15 minutes. After a further 15 minutes, a solution of 3.06 g. (20 mMol) 5-amino-1,2,3,4-tetrazole and 20 ml. dimethylformamide are added dropwise thereto within the course of 15 minutes. After stirring for 1 hour at -10° C., the reaction mixture is allowed to come to ambient temperature overnight, the solvent is distilled off, the oily residue is taken up in ethyl acetate and shaken out with 2N aqueous sodium hydroxide solution. The aqueous alkaline phases are acidified with 2N sulphuric acid and the resultant precipitate is filtered off with suction and thoroughly washed with water. After crystallisation from ethanol, there are obtained 4.20 g. (48% of theory) of colourless crystals; m.p. 227.5°-229.5° C.

Workup

  1. additionTo a suspension of 7.30 g
  2. customwithin the course of 15 minutes
  3. customwithin the course of 15 minutes
  4. waitto come to ambient temperature overnight
  5. distillationthe solvent is distilled off
  6. stirringshaken out with 2N aqueous sodium hydroxide solution
  7. filtrationthe resultant precipitate is filtered off with suction
  8. washthoroughly washed with water
  9. customAfter crystallisation from ethanol, there
  10. customare obtained 4.20 g

Sources & evidence

ORD record
ord-db87946a56c943fa9246d44ee607010f
Source dataset
uspto-grants-1992_12
Patent number
US05173500

Reaction notes

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