m-Chlorophenylhydrazine hydrochloride → N-[(E)-3-[tert-butyl(diphenyl)silyl]oxypropylideneamino]-3-chloroaniline

HRID 1508322Notes

Reaction equation

HRID 1508322 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[Si:11]([O:28][CH2:29][CH2:30][CH:31]=O)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Si:11]([O:28][CH2:29][CH2:30]/[CH:31]=[N:10]/[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=1)([C:24]([CH3:25])([CH3:26])[CH3:27])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 9995679Propanal, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

Product 1

HCID 89405959N-[(E)-3-[tert-butyl(diphenyl)silyl]oxypropylideneamino]-3-chloroaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3-chlorophenyl)hydrazine hydrochloride and TEA (3 mL, 21.5 mmol) and 3-(tert-butyldiphenylsilyloxy)propanal (21.5 mmol) in toluene was stirred at rt overnight. The reaction mixture was then quenched with H2O (100 mL) and extracted with EtOAc (2×). The organic layers were dried (MgSO4) and evaporated to a reddish oil. The crude product was then purified using silica gel chromatography. The desired product was isolated as a red oil. MS(ESI) m/z: 437.1 (M-Boc)+. 1H NMR (400 MHz, CDCl3) δ 7.84-7.59 (m, 4H), 7.50-7.29 (m, 6H), 7.18-6.90 (m, 1H), 6.77 (dt, J=8.1, 2.0 Hz, 1H), 3.98-3.68 (m, 2H), 2.63-2.38 (m, 2H), 1.12-0.90 (m, 9H) ppm.

Workup

  1. customThe reaction mixture was then quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. customevaporated to a reddish oil
  5. customThe crude product was then purified

Sources & evidence

ORD record
ord-00179d9cf47f4383821d463ab440c519
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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