Morpholine → HCID 13013931, compound

HRID 444145Notes

Reaction equation

HRID 444145 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[N:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(#N)C>[O:24]1[CH2:25][CH2:26][N:21]([C:2]2[C:8]3[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=3[S:6][C:5]3[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=3[N:3]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 13013926HCID 13013926, compound

Product 1

HCID 13013931HCID 13013931, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux a mixture of 3.035 gm. (10 mmole) of the 11-chloro ester of Example 6, 2.61 mg. (30 mmmole) of morpholine and 30 ml. of dry acetonitrile under an argon atmosphere for 40 hours. Add 50 ml. of ice-water to the reaction mixture and extract twice with 50 ml. portions of ethyl acetate. Wash the combined extracts with 50 ml. of water and then with 50 ml. of saturated aqueous sodium chloride solution. Dry over magnesium sulfate and evaporate. Chromatograph the residue over silica gel eluting with 1:9 ethyl acetate in toluene. Recrystallize from diisopropyl ether to obtain the title product, (m.p. 114°-115° C.).

Workup

  1. temperatureReflux
  2. additiona mixture of 3.035 gm
  3. additionAdd 50 ml
  4. extractionof ice-water to the reaction mixture and extract twice with 50 ml
  5. washWash the combined extracts with 50 ml
  6. dry with materialDry over magnesium sulfate
  7. customevaporate
  8. customRecrystallize from diisopropyl ether

Sources & evidence

ORD record
ord-39f6bd4293c3471faa96e769f9f58579
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

Loading…