2-Chloropropionyl chloride → HCID 22603045, compound

HRID 1019071Notes

Reaction equation

HRID 1019071 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[C:22](=[O:26])[CH:23]([Cl:25])[CH3:24]>ClCCCl>[S:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[NH:11][C:5]1[CH:6]=[CH:7][C:8]([C:22](=[O:26])[CH:23]([Cl:25])[CH3:24])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 1110192-Chloropropionyl chlorideHCID 230981AnilinobenzothiazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22603045HCID 22603045, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Aluminium(III)chloride (0.666 mol) was added portionwise at RT to a solution of N-phenyl-2-benzothiazolylamine (0.222 mol) and 1,2-dichloro-1-propanone (0.233 mol) in 1,2-dichloroethane (500 ml) and the mixture was stirred and heated at 80° C. for 2 hours. The mixture was poured into ice and extracted with CH2Cl2. The organic layer was decanted, dried filtered and the solvent was evaporated, yielding 68 g of (±)-1-[4-(2-benzothiazolylamino)phenyl]-2-chloro-1-propanone (95.7%) (interm. 22).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was decanted
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b91848250e354535bd855a12a131fbb4
Source dataset
uspto-grants-2002_11
Patent number
US06486187B1

Reaction notes

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