Hydrochloric Acid → HCID 53922348, compound

HRID 2107173Notes

Reaction equation

HRID 2107173 reaction equation
O.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[C:14]2[S:18][C:17](=[S:19])[N:16]([CH2:20][C:21]([OH:23])=[O:22])[C:15]2=[O:24])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.Cl>CN(C)P(=O)(N(C)C)N(C)C>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[C:14]2[S:18][C:17](=[S:19])[N:16]([CH2:20][C:21]([O:23][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:22])[C:15]2=[O:24])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 86744020HCID 86744020, compound

Product 1

HCID 53922348HCID 53922348, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture comprising 2 g of 5-[1-(2-aminothiazol-4-yl)-1-ethoxycarbonylmethylene]rhodanine-3-acetic acid monohydrate, 3 g of benzyl bromide, 1.1 g of triethylamine and 10 ml of hexamethylphosphoric triamide was stirred at room temperature for 16 hours. The reaction mixture was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography using as eluent a 8:2:1 by volume mixture of hexane, ethyl acetate and acetic acid, giving the desired compound as yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additionby volume mixture of hexane, ethyl acetate and acetic acid

Sources & evidence

ORD record
ord-1a66623898d242a5a5dedccc93337ddc
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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