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Potassium Carbonate → Ethyl 2-{4-[2-(6-(3-chlorobenzoyl)-2-oxo-1,3-benzothiazol-3(2H)-yl)-ethoxy]phenoxy}-2-methylpropanoate

HRID 1790268
Notes
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Reaction equation

HRID 1790268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[CH:12][S:13](=O)[C:9]=2[CH:8]=1)=[O:6].C([O-])([O-])=[O:21].[K+].[K+].Cl[CH2:27][CH2:28][O:29][C:30]1[CH:44]=[CH:43][C:33]([O:34][C:35]([CH3:42])([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][CH:31]=1.[OH-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[CH:16]=[CH:15][C:10]2[N:11]([CH2:27][CH2:28][O:29][C:30]3[CH:44]=[CH:43][C:33]([O:34][C:35]([CH3:42])([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][CH:31]=3)[C:12](=[O:21])[S:13][C:9]=2[CH:8]=1)=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 22041517HCID 22041517, compoundHCID 1317258326-(3'-Chlorobenzoyl)-benzothiazolinone

Product 1

HCID 22041531Ethyl 2-{4-[2-(6-(3-chlorobenzoyl)-2-oxo-1,3-benzothiazol-3(2H)-yl)-ethoxy]phenoxy}-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution, heated at 80° C. for 2 hours, of 6-(3′-chlorobenzoyl)-benzothiazolinone (1.8 g) in the presence of K2CO3 (1.72 g) in 20 ml of DMF there is added ethyl 2-[4-(2-chloroethoxy)phenoxy]-2-methylpropanoate (1.96 g). The reaction mixture is heated at 120° C. for 5 days, cooled, hydrolysed using 100 ml of water and rendered alkaline using 1N NaOH. The precipitate obtained is filtered off and then recrystallised from cyclohexane to yield the title compound in the form of a white powder.

Workup

  1. temperaturecooled
  2. customThe precipitate obtained
  3. filtrationis filtered off
  4. customrecrystallised from cyclohexane

Sources & evidence

ORD record
ord-82f2de4777404c1f83fd80eb7ede4828
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071221B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes