4-(Hydroxymethyl)benzoic acid → 4-(Hydroxymethyl)-N'-(4-isobutylbenzoyl)benzohydrazide

HRID 2242235Notes

Reaction equation

HRID 2242235 reaction equation
[CH2:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH:11][NH2:12])=[O:10])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CN(C=O)C>[OH:22][CH2:21][C:20]1[CH:24]=[CH:25][C:17]([C:16]([NH:12][NH:11][C:9](=[O:10])[C:8]2[CH:13]=[CH:14][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=2)=[O:15])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 763604-(Hydroxymethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 207719354-Isobutylbenzohydrazide

Product 1

HCID 592043014-(Hydroxymethyl)-N'-(4-isobutylbenzoyl)benzohydrazideYield 56.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Isobutylbenzohydrazide (2.10 g, 10.9 mmol) was added to a stirred solution of 4-hydroxymethylbenzoic acid (1.66 g, 11.2 mmol), HBTU (4.25 g, 11.2 mmol), diisopropylethylamine (1.45 g, 11.2 mmol) and DMF (50 mL) and stirred at room temperature for 12 hours. The reaction was diluted with ethyl acetate (200 mL), washed with 5% NaHCO3 (aq.) and brine, dried (MgSO4), filtered and concentrated in vacuo to give a white solid. The solid was triturated with ethyl acetate and filtered to give the title compound (2.01 g, 56% yield).

Workup

  1. washwashed with 5% NaHCO3 (aq.) and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a white solid
  6. customThe solid was triturated with ethyl acetate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-03a62edc31ae4999a21ee6340e8aa86f
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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