Benzene → HCID 15053528, compound

HRID 2107244Notes

Reaction equation

HRID 2107244 reaction equation
C1C=CC=CC=1.[CH3:7][NH:8][CH3:9].Cl[C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:15]=1.O1CCCC1>O>[CH3:7][N:8]([CH3:9])[C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:15]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 451176154-Thiazoleaceticacid,2-chloro--alpha--oxo-,ethylester(9CI)

Product 1

HCID 15053528HCID 15053528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 10 ml of a 2M benzene solution of dimethylamine, 1.3 g of ethyl 2-chlorothiazol-4-ylglyoxylate, and 5 ml of tetrahydrofuran was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, using as eluent a 9:1 by volume mixture of benzene and ethyl acetate, giving the title compound as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. additionby volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-dab4ba335e9a4b60b6591983d72cac53
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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