3-Chloropropionyl chloride → HCID 23287870, compound

HRID 1417035Notes

Reaction equation

HRID 1417035 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[NH:11][C:4]=2[CH:3]=1.[Cl:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]([C:21](=[O:22])[CH2:20][CH2:19][Cl:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 13497198HCID 13497198, compound

Product 1

HCID 23287870HCID 23287870, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-chloro-12H-dibenzo[d,g][1,3,6]dioxazocine (10.65 g, 43 mmol, prepared as described in Journal of Molecular Structures, 131, 1985, 131-140) and 3chloropropionyl chloride (6.55 g, 51.6 mmol) in dry toluene (100 ml) was heated at reflux temperature for 5 h. After cooling to room temperature, the reaction mixture was washed with a saturated solution of sodium bicarbonate (50 ml). The organic layer was dried (MgSO4), and evaporated in vacuo, which afforded 2-chloro-12-(3-chloropropionyl)-12H-dibenzo[d,g][1,3,6]dioxazocine (12.9 g, 88%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 h
  3. washthe reaction mixture was washed with a saturated solution of sodium bicarbonate (50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated in vacuo, which

Sources & evidence

ORD record
ord-4c26745d9c234365ae9ee05f77f6f88a
Source dataset
uspto-grants-1999_06
Patent number
US05917047

Reaction notes

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