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Diisopropylethylamine → 4-allyloxy-3,5-dimethyl-benzoic acid N'-(5-isobutyl-thiophene-2-carbonyl)-hydrazide

HRID 1094304
Notes
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Reaction equation

HRID 1094304 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:44]([O:47][C:48]1[C:57]([CH3:58])=[CH:56][C:51]([C:52]([NH:54][NH2:55])=[O:53])=[CH:50][C:49]=1[CH3:59])[CH:45]=[CH2:46]>C(Cl)Cl.CCOCC>[CH2:1]([C:5]1[S:9][C:8]([C:10]([NH:55][NH:54][C:52](=[O:53])[C:51]2[CH:50]=[C:49]([CH3:59])[C:48]([O:47][CH2:44][CH:45]=[CH2:46])=[C:57]([CH3:58])[CH:56]=2)=[O:12])=[CH:7][CH:6]=1)[CH:2]([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 196226895-(2-Methylpropyl)thiophene-2-carboxylic acidHCID 592020394-Allyloxy-3,5-dimethyl-benzoic acid hydrazide

Product 1

HCID 666369514-allyloxy-3,5-dimethyl-benzoic acid N'-(5-isobutyl-thiophene-2-carbonyl)-hydrazide
Yield 80.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-isobutyl-thiophene-2-carboxylic acid (830 mg, 4.51 mmol) and DIPEA (680 mg, 5.27 mmol) in DCM (20 mL) is added TBTU (1.59 g, 4.96 mmol) at rt. The mixture is stirred at rt for 45 min before 4-allyloxy-3,5-dimethyl-benzoic acid hydrazide (993 mg, 4.50 mmol) is added. Stirring is continued for 2 h. The mixture is diluted with ether (200 mL) and washed with 1M aq. HCl (3×50 mL), 1M aq. NaOH (3×50 mL) and brine (50 mL). The org. extract is dried over MgSO4, filtered and evaporated to give the crude 4-allyloxy-3,5-dimethyl-benzoic acid N′-(5-isobutyl-thiophene-2-carbonyl)-hydrazide (1.40 g) as a yellow oil that slowly solidifies; LC-MS: tR=1.02 min, [M+1]+=387.10.

Workup

  1. additionis added
  2. washwashed with 1M aq. HCl (3×50 mL), 1M aq. NaOH (3×50 mL) and brine (50 mL)
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4257db04a7554dfa812ac90998635693
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133910B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes