Aluminium lithium hydride → 4-Chlorophenylurea

HRID 857136

Reaction equation

HRID 857136 reaction equation
C(C1C=C([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])N(C2C=C(C=CC=2)C(OCC)=O)N=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:11](=[O:12])[NH2:10])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21867337Ethyl 3-{3-t-butyl-5-[3-(4-chlorophenyl)ureido]-1h-pyrazol-1-yl}benzoate

Product 1

HCID 87964-ChlorophenylureaYield 226.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example C (1.60 g, 3.63 mmol) in THF (200 mL) was added LiAlH4 powder (413 mg, 10.9 mmol) at −10° C. under N2. The mixture was stirred for 2 h and excess LiAlH4 was quenched by adding ice. The solution was acidified to pH=7 with dilute HCl. Solvents were slowly removed and the solid was filtered and washed with EtOAc (200+100 mL). The filtrate was concentrated to yield 1-{3-tert-butyl-1-[3-hydroxymethyl)phenyl]-1H-pyrazol-5-yl}-3-(4-chlorophenyl)urea (1.40 g, 97%). 1H NMR (DMSO-d6): δ 9.11 (s, 1H), 8.47 (s, 1H), 7.47–7.27 (m, 8H), 6.35 (s, 1H), 5.30 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H), 1.26 (s, 9H); MS (ESI) m/z: 399 (M+H+).

Workup

  1. customexcess LiAlH4 was quenched
  2. additionby adding ice
  3. customSolvents were slowly removed
  4. filtrationthe solid was filtered
  5. washwashed with EtOAc (200+100 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a4e474a4974746afb23ddce41686373e
Source dataset
uspto-grants-2006_12
Patent number
US07144911B2

Linked notes

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