4-Chlorobutyryl chloride → HCID 21471973, compound

HRID 1734036Notes

Reaction equation

HRID 1734036 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[CH2:9][CH2:8][CH2:7][NH:6][C:5](=[O:12])[C:4]=2[CH:3]=1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([C:3]1[C:4]2[C:5](=[O:12])[NH:6][CH2:7][CH2:8][CH2:9][C:10]=2[S:11][C:2]=1[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21471960HCID 21471960, compound

Product 1

HCID 21471973HCID 21471973, compoundYield 15.2%

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-c]azepin-4-one and 5 g of 4-chlorobutyryl chloride in 50 ml of dichloroethane was added 8.6 g of aluminum chloride under ice-cooling 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 1.2 g of 3-(4-chlorobutyryl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepin-4-one as white crystals, m.p. 113°-115° C.

Workup

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

Sources & evidence

ORD record
ord-68489657fd1a4c4699028b322d42078b
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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