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Dimethylformamide → 2-(4-Benzyloxy-3-methoxyphenyl)benzothiazole

HRID 340659
Notes
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Reaction equation

HRID 340659 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)(Cl)=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[SH:36]>C(Cl)Cl.N1C=CC=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[S:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 87132-AminothiophenolHCID 24386Thionyl ChlorideHCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

Product 1

HCID 669113302-(4-Benzyloxy-3-methoxyphenyl)benzothiazole

Reagents, catalysts & solvents 4

HCID 962Water
Solvent
2×
HCID 1049PyridineSolvent
HCID 1140TolueneSolvent2×
HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

In methylene chloride (10 ml) was suspended 2.0 g (7.7 mmol) of 4-benzyloxy-3-methoxy benzoic acid. To this suspension was added 0.05 g of DMF and 0.68 ml of thionyl chloride, followed by stirring at 50° C. for 2 hours. This reaction solution was introduced dropwise at 0° C. into a solution wherein 1.2 g (9.3 mmol) of 2-aminothiophenol had been dissolved in 10 ml of pyridine at room temperature. The mixture was further stirred overnight at room temperature, diluted with water, and subjected to ethyl acetate extraction (50 ml×2 times). The extracts were dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue thus obtained was dissolved in 30 ml of toluene. This toluene solution was heated to reflux overnight while water was distilled off. Toluene was removed from this solution by distillation under reduced pressure, and the residue was purified using a silica gel column (eluant:ethyl acetate/hexane=1/5). The solvent was distilled off under reduced pressure. Using the crystals thus obtained, the desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane.

Workup

  1. waitThe mixture was further stirred overnight at room temperature
  2. extractionsubjected to ethyl acetate extraction (50 ml×2 times)
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue thus obtained
  6. distillationwas distilled off
  7. customToluene was removed from this solution by distillation under reduced pressure
  8. customthe residue was purified
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthus obtained
  11. customthe desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane

Sources & evidence

ORD record
ord-601a2c7cf5f540bf80d41a7047f198a8
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895599B2

Reaction notes

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