Acetyl chloride → HCID 12850687, compound

HRID 1065099Notes

Reaction equation

HRID 1065099 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:16][CH2:15][CH2:14][CH2:13][S:12][CH:11]([CH3:17])[C:10]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([N:16]1[C:9]2[CH:8]=[CH:7][C:6]([Cl:5])=[CH:18][C:10]=2[CH:11]([CH3:17])[S:12][CH2:13][CH2:14][CH2:15]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 12850672HCID 12850672, compound

Product 1

HCID 12850687HCID 12850687, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4 g of acetyl chloride were added dropwise to a suspension of 11.4 g of 8-chloro-1,3,4,6-tetrahydro-6-methyl-2H-5,1-benzothiazocine and 10 g of potassium carbonate in 100 ml of acetone, whilst keeping the temperature of the mixture below 10° C. The mixture was stirred for 30 minutes, after which it was poured into ice-water and extracted with chloroform. The solvent was evaporated from the extract and the residue was recrystallized from a 3:2 by volume mixture of methylene chloride and n-hexane to give 5 g of 1-acetyl-8-chloro-1,3,4,6-tetrahydro-6-methyl-2H-5,1-benzothiazocine in the form of crystals melting at 132°-135° C.

Workup

  1. customthe temperature of the mixture below 10° C
  2. extractionextracted with chloroform
  3. customThe solvent was evaporated from the
  4. extractionextract
  5. customthe residue was recrystallized from a 3:2 by volume mixture of methylene chloride and n-hexane

Sources & evidence

ORD record
ord-a3c4526743ac470ba85cb46248888e2f
Source dataset
uspto-grants-1982_05
Patent number
US04328238

Reaction notes

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