1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (4-Benzyloxy-phenyl)-acetic acid hydrazide

HRID 1927249Notes

Reaction equation

HRID 1927249 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:40]=[N:39]C=2C=1>O.C(N(CC)CC)C.C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:39][NH2:40])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acid

Product 1

HCID 59287387(4-Benzyloxy-phenyl)-acetic acid hydrazideYield 16.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of THF (50 mL) of 4-benzyloxy-phenylacetic acid (7.0 g) were added hydrazine monohydrate (4.3 g), WSC (6.7 g), HOBt (4.7 g), and triethylamine (3.5 g), which was stirred for 15 hours at room temperature. Water was added to the reaction mixture, and the precipitated solids were filtered off to obtain the titled compound (1.2 g).

Workup

  1. filtrationthe precipitated solids were filtered off

Sources & evidence

ORD record
ord-24b96b4c1d894617bd44b1326dfa6a2e
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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