Chloroform → HCID 14328128, compound

HRID 330067Notes

Reaction equation

HRID 330067 reaction equation
C(N(CC)CC)C.C(O[O:12][C:13]1[C:18]([CH3:19])=[N:17][C:16]([CH3:20])=[C:15]([CH3:21])[N:14]=1)(=O)C.C(Cl)(Cl)Cl.Br.[Br:27][CH2:28][CH2:29][NH2:30].[O:31]1CC[CH2:33][CH2:32]1>>[Br:27][CH2:28][CH2:29][NH:30][C:32](=[O:31])[CH2:33][O:12][C:13]1[C:18]([CH3:19])=[N:17][C:16]([CH3:20])=[C:15]([CH3:21])[N:14]=1

Participants

6

Reactant 5

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 27742172-Bromoethylamine hydrobromideHCID 23200466HCID 23200466, compound

Product 1

HCID 14328128HCID 14328128, compound

Procedure

Triethylamine (7.0 ml, 50 mM) was added to compound 037 (9.80 g, 50 mM) dissolved in tetrahydrofuran (100 ml) and chloroform (100 ml) in solution with bromoethylamine hydrobromide (10.30 g, 50 mM) and triethylamine (7.7 ml, 55 mM) was added dropwise at -5° C., then the mixture was stirred for 4 hours with ice cooling. The reaction mixture was concentrated in vacuo, the residue was dissolved in chloroform and washed with dilute aqueous potassium carbonate. The aqueous layer was extracted with chloroform. The organic layer was combined, dried with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was charged on a column of silica gel (Chlodil, 250 g), and eluted successively with chloroform and chloroform-methanol (500:1) to obtain the product (6.92 g)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with dilute aqueous potassium carbonate
  4. extractionThe aqueous layer was extracted with chloroform
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additionThe residue was charged on a column of silica gel (Chlodil, 250 g)
  8. washeluted successively with chloroform and chloroform-methanol (500:1)

Sources & evidence

ORD record
ord-c8ad7efba6434ed2a7d7ac7e65a669b5
Source dataset
uspto-grants-1990_01
Patent number
US04894453

Reaction notes

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