Triethylamine → 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide

HRID 1666596Notes

Reaction equation

HRID 1666596 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH3:19])=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][C:10]=1[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:29]([O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][C:34]=1[CH3:42])([CH3:31])[CH3:30]>C(Cl)Cl.CC(=O)OCC>[CH:29]([O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:16][NH:15][C:13](=[O:14])[C:12]2[CH:17]=[C:18]([CH3:19])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([CH2:20][CH3:21])[CH:11]=2)=[O:38])=[CH:35][C:34]=1[CH3:42])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 592020264-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazideHCID 874026094-Isopropoxy-3-methyl-benzoyl chloride

Product 1

HCID 674440334-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazideYield 103.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide (1.12 g, 3.95 mmol) in DCM (20 mL), triethylamine (500 mg, 4.94 mmol) is added. The clear solution is cooled to 5° C. before a solution of 4-isopropoxy-3-methyl-benzoic acid chloride (700 mg, 3.29 mmol) in DCM (10 mL) is added dropwise. The suspension is stirred at rt for 1 h before it is diluted with EA, washed with 1 N aq. HCl, followed by water, dried over MgSO4, filtered, concentrated and dried to give 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide (1.57 g) as a white solid; LC-MS: tR=1.05 min, [M+1]+=461.66.

Workup

  1. additionis added
  2. additionis added dropwise
  3. washwashed with 1 N aq. HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-8638dfb68e92432eb84713cadc736ed7
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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