Thionyl Chloride → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide

HRID 1666590Notes

Reaction equation

HRID 1666590 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.O.[NH2:26][NH2:27]>C(Cl)(Cl)Cl.C1COCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13]([NH:26][NH2:27])=[O:14])=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acid

Product 1

HCID 592020264-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazideYield 23.7%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-3-ethyl-5-methylbenzoic acid (4.38 g, 17.2 mmol) in chloroform (60 mL), thionylchloride (5 mL, 68.9 mmol) is added. The mixture is refluxed for 2.5 h before the solvent is evaporated in vacuo. The remaining red oil is dissolved in THF (150 mL) and then added dropwise to a solution of hydrazine hydrate (3.46 g, 69.3 mmol) in THF (80 mL). The mixture is stirred 2 h at rt, diluted with diethyl ether, washed with 1 N aq. HCl, dried over MgSO4, filtered, concentrated and dried to give 4-benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide (1.16 g) as a white solid; LC-MS: tR=0.82 min, [M+1]+=285.47, 1H NMR (CDCl3): δ 0.98 (t, J=7.3 Hz, 3H), 1.98 (s, 3H), 2.39 (q, J=7.3 Hz, 2H), 4.49 (s, 2H), 7.20-7.32 (m, 5H) 7.57 (s, 1H), 7.65 (s, 1H), 11.23 (s, 1H).

Workup

  1. temperatureThe mixture is refluxed for 2.5 h before the solvent
  2. customis evaporated in vacuo
  3. dissolutionThe remaining red oil is dissolved in THF (150 mL)
  4. washwashed with 1 N aq. HCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-781b6ebead6c47c199432dc50e62ec17
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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