3-Chloropropionyl chloride → HCID 21471943, compound

HRID 2294808Notes

Reaction equation

HRID 2294808 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:12])[NH:5][C:4]=2[CH:3]=1.[Cl:13][CH2:14][CH2:15][C:16](Cl)=[O:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:13][CH2:14][CH2:15][C:16]([C:3]1[C:4]2[NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][C:10]=2[S:11][C:2]=1[CH3:1])=[O:17]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21471838HCID 21471838, compound

Product 1

HCID 21471943HCID 21471943, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 5 g of 2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-5-one and 4.5 g of 3-chloropropionyl chloride in 50 ml of dichloroethane was added 9.2 g of aluminum chloride and the mixture was stirred for 3 hours. The mixture was poured into ice-cold water and extracted with chloroform. The organic layer was washed with saline solution, dried over magnesium sulfate and concentrated. The residue was recrystallized from ethanol to give 5.6 g of 3-(3-chloropropionyl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-5-one as white crystals, m.p. 86°-87° C.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saline solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7e871bbdc5c24f1c8f1ccfc53f00a067
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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