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Hydrochloric Acid → 4-[2-(7-Chloromethyl-benzo[b]thiophen-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 353673
Notes
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Reaction equation

HRID 353673 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([O:10][CH2:11][CH2:12][C:13]3[N:14]=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:16][C:17]=3[CH3:18])=[CH:7][CH:8]=[CH:9][C:2]1=2.O1CC[CH2:28]OO1.[ClH:31]>ClCCl>[Cl:31][CH2:28][C:9]1[C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 112329474-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzothiopheneHCID 19593658CID 19593658

Product 1

HCID 235144434-[2-(7-Chloromethyl-benzo[b]thiophen-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 335 mg of 4-[2-(Benzo[b]thiophene-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole (1 mmol) and 110 mg of Trioxane (3.6 mmol) in 15 ml dichloromethane was treated with 2 ml of 37% HCl solution and saturated for 10 min with HCl gas and reacted at 2° C. for 23 h. The resulting mixture was extracted wich 10% sodium carbonate solution and water and evaporated to dryness. Digestion with tert. butyl methylether at room temperature left a light brown residue (0.11 g) consisting of 4-[2-(7-Chloromethyl-benzo[b]thiophen-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole with a m.p. of 144-145° C.

Workup

  1. customreacted at 2° C. for 23 h
  2. extractionThe resulting mixture was extracted wich 10% sodium carbonate solution and water
  3. customevaporated to dryness
  4. waitDigestion with tert. butyl methylether at room temperature left a light brown residue (0.11 g)

Sources & evidence

ORD record
ord-f770e9f5b1bd494484cbd0e8c280659d
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06753432B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes