Stannous chloride dihydrate → HCID 18184540, compound

HRID 1358459Notes

Reaction equation

HRID 1358459 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][C:30]=1[N+:31]([O-])=O)[CH2:12][CH2:13][NH:14][C:15](=[O:27])[CH2:16][C:17]1[CH:22]=[C:21]([Br:23])[C:20]([O:24][CH3:25])=[C:19]([Br:26])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C.Cl>[NH2:31][C:30]1[CH:29]=[CH:28][C:11]([CH2:12][CH2:13][NH:14][C:15](=[O:27])[CH2:16][C:17]2[CH:22]=[C:21]([Br:23])[C:20]([O:24][CH3:25])=[C:19]([Br:26])[CH:18]=2)=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 18184509HCID 18184509, compound

Product 1

HCID 18184540HCID 18184540, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-(3-Benzyloxy-4-nitrophenethyl)-3,5-dibromo-4-methoxy-phenylacetamide (3.49 g, 0.006 mol) and tin (II) chloride dihydrate (16.10 g, 0.071 mol) in a mixture of ethanol (300 mL) and 1.2 N HCl (150 mL) was refluxed for 3h, cooled and concentrated. Tin salts were dissolved in 1N NaOH solution. The reaction mixture was extracted with methylene chloride 3 times. The extracts were dried over Na2SO4 and concentrated. A residue was crystallized from ethyl acetate-hexanes mixture. Yield 1.57 g (47.4%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionTin salts were dissolved in 1N NaOH solution
  4. extractionThe reaction mixture was extracted with methylene chloride 3 times
  5. dry with materialThe extracts were dried over Na2SO4
  6. concentrationconcentrated
  7. customA residue was crystallized from ethyl acetate-hexanes mixture

Sources & evidence

ORD record
ord-cdc254b5766a4ef4a5c3c027196c0c52
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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