Hydrazine hydrate (1:1) → 9-Fluorenylmethyl carbazate

HRID 518906Notes

Reaction equation

HRID 518906 reaction equation
O.[NH2:2][NH2:3].[C:4](Cl)([O:6][CH2:7][CH:8]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:5]>CC#N.O.CC#N>[C:4]([O:6][CH2:7][CH:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)(=[O:5])[NH:2][NH2:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 1618839-Fluorenylmethyl carbazate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a well-stirred solution of hydrazine hydrate (19 g, 386 mmol) in 150 mL of CH3CN/H2O (1/1, v/v), a solution of FmocCl (10 g, 38.65 mmol) in 600 mL CH3CN was added dropwise at 0° C. over 2 h. The reaction mixture was then allowed to warm to room temperature and stirred for an additional 12 hours, concentrated in vacuo to 150 mL and filtered to yield the title compound as a white solid, which was washed with water and hexane and dried to a constant weight in vacuo (9.74 g, 99%): mp 172-173° C.; 1H NMR (DMSO) □ 4.08 (brs, 2H), 4.21 (t, J=7.2 Hz, 1H), 4.28 (d, J=7.2 Hz, 2H), 7.32 (t, J=7.4 Hz, 2H), 7.42 (t, J=7.4 Hz, 2H), 7.69 (d, J=7.4 Hz, 2H), 7.89 (d, J=7.4 Hz, 2H), 8.36 (brs, 1H); 13C NMR (DMSO) □□ 47.7, 66.7, 121.1 (2C), 126.3 (2C), 128.1 (2C), 128.7 (2C), 141.7 (2C), 144.9 (2C), 159.2.

Workup

  1. concentrationconcentrated in vacuo to 150 mL
  2. filtrationfiltered

Sources & evidence

ORD record
ord-0010df79c2054e808dce4bb299120310
Source dataset
uspto-grants-2015_08
Patent number
US09115171B2

Reaction notes

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