Ethoxalyl chloride → HCID 20482445, compound

HRID 648217Notes

Reaction equation

HRID 648217 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[N:6]=1.[C:27](Cl)([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:28]>O1CCCC1.N1C=CC=CC=1>[CH:14]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:28])[S:3][CH:4]=2)[CH2:9][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 13386489HCID 13386489, compound

Product 1

HCID 20482445HCID 20482445, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-(4-benzhydrylpiperazin-1-ylmethyl)thiazole (1.8 g) in tetrahydrofuran (5 ml) and pyridine (10 ml) was added dropwise ethoxalyl chloride (1.1 g) under ice-cooling with stirring, and the stirring was continued at the same temperature for an hour. After concentration of the reaction mixture, the residue was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and then evaporated to dryness to give a residue, which was chromatographed on silica gel using ethyl acetate as an eluent. The eluates containing the desired compound were collected and evaporated, followed by recrystallization from a mixture of ethyl acetate and n-hexane to obtain pale yellow crystals (0.7 g) of 4-(4-benzhydrylpiperazin-1-ylmethyl)-2-ethoxalylaminothiazole, mp 125°-128° C.

Workup

  1. temperaturecooling
  2. waitthe stirring was continued at the same temperature for an hour
  3. extractionAfter concentration of the reaction mixture, the residue was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customto give a residue, which
  8. customwas chromatographed on silica gel
  9. additionThe eluates containing the desired compound
  10. customwere collected
  11. customevaporated
  12. customfollowed by recrystallization from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-c3ee0f6a8d5e43fa9e28d946bc532670
Source dataset
uspto-grants-1983_10
Patent number
US04411900

Reaction notes

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