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Acetic Anhydride → N-{(2E)-3-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-enyl}acetamide

HRID 2078454
Notes
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Reaction equation

HRID 2078454 reaction equation
[N:1]([CH:4]([CH3:23])/[CH:5]=[CH:6]/[C:7]1[S:11][C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)=[N:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].[C:45](OC(=O)C)(=[O:47])[CH3:46]>O1CCCC1>[CH:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]2[S:11][C:7](/[CH:6]=[CH:5]/[CH:4]([NH:1][C:45](=[O:47])[CH3:46])[CH3:23])=[CH:8][N:9]=2)=[CH:14][CH:15]=1)([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 866212085-[(1E)-3-azidobut-1-enyl]-2-(4-isopropoxyphenoxy)-1,3-thiazole

Product 1

HCID 25152671N-{(2E)-3-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-enyl}acetamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 7F (85 mg, 0.26 mmole) in tetrahydrofuran (3 mL)) was added triphenylphosphine (75 mg, 0.29 mmole) and stirred at 50° C. for 3.5 hours. The reaction mixture was added an aqueous solution of 2N NaOH (0.3 mL) and stirring was continued at 50° C. for additional 40 minutes. The reaction mixture was cooled down to room temperature, added acetic anhydride (200 μL, 2.1 mmole), stirred for 45 minutes, quenched with methanol and stirred at room temperature, overnight. The reaction mixture was diluted with methylene chloride and washed with water (×3) and brine. The product was purified via silica column, using a gradient of 25-100% ethyl acetate in hexane and yielded 40 mg (44.9%) of light yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.11-7.22 (m, 2H) 7.04 (s, 1H) 6.85-6.95 (m, 2H) 6.48 (dd, J=15.44, 1.10 Hz, 1H) 5.72 (dd, J=15.63, 5.70 Hz, 1H) 5.37 (d, J=8.46 Hz, 1H) 4.60-4.76 (m, 1H) 4.44-4.59 (m, 1H) 2.00 (s, 3H) 1.34 (d, J=6.25 Hz, 6H) 1.28 (d, J=6.62 Hz, 3H). Mass spectrum DCI 347 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued at 50° C. for additional 40 minutes
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. stirringstirred for 45 minutes
  5. customquenched with methanol
  6. stirringstirred at room temperature, overnight
  7. additionThe reaction mixture was diluted with methylene chloride
  8. washwashed with water (×3) and brine
  9. customThe product was purified via silica column
  10. customyielded 40 mg (44.9%) of light yellow oil

Sources & evidence

ORD record
ord-eea1d0341a474b2592e7e8400c4bc01a
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928243B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes