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Diethyl Ether → 5-[(1E)-3-azidobut-1-enyl]-2-(4-isopropoxyphenoxy)-1,3-thiazole

HRID 2078453
Notes
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Reaction equation

HRID 2078453 reaction equation
C(O[CH:5]([CH3:24])/[CH:6]=[CH:7]/[C:8]1[S:12][C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[N:10][CH:9]=1)(=O)C.[N-:25]=[N+:26]=[N-:27].[Na+].CCOCC.CCCCCC>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:25]([CH:5]([CH3:24])/[CH:6]=[CH:7]/[C:8]1[S:12][C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[N:10][CH:9]=1)=[N+:26]=[N-:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 33557Sodium Azide3×HCID 67096975(2E)-3-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-enyl acetate

Product 1

HCID 866212085-[(1E)-3-azidobut-1-enyl]-2-(4-isopropoxyphenoxy)-1,3-thiazoleYield 57.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 7E (155 mg, 0.45 mmole) in tetrahydrofuran (15 mL) was added sodium azide (32 mg, 0.5 mmole) and tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.022 mmole) and heated at 50° C. After 2 hours additional sodium azide (23 mg, 0.35 mmole) was added and after 8 hours a third amount of sodium azide (40 mg, 0.61 mmole) was added and stirred at 50° C. overnight. The reaction mixture was added ether and hexane and the organic phase was washed twice with water followed by brine. The reaction mixture was dried over magnesium sulfate filtered and evaporated. The product was purified via silica column, using a gradient of 5-25% ethyl acetate in hexane and yielded 85 mg (57.6%) of clear oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.13-7.22 (m, 2H) 7.10 (s, 1H) 6.86-6.98 (m, 2H) 6.58 (d, J=15.44 Hz, 1H) 5.69 (dd, J=15.63, 7.17 Hz, 1H) 4.42-4.62 (m, 1H) 3.96-4.23 (m, 1H) 1.35 (d, J=5.88 Hz, 6H) 1.33 (d, J=5.88 Hz, 3H). Mass spectrum DCI 331 (M+H)+.

Workup

  1. additionwas added
  2. washthe organic phase was washed twice with water
  3. dry with materialThe reaction mixture was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was purified via silica column

Sources & evidence

ORD record
ord-34725e1695e94e9e96083f0589fdc7be
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