Aluminium lithium hydride → 1-(3,4-Dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea

HRID 1685030Notes

Reaction equation

HRID 1685030 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7](=[O:20])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](N(OC)C)=[O:15])[N:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]=[O:15])[N:13]=1)=[O:20]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866612922-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide

Product 1

HCID 866227621-(3,4-Dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 g of 2-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide was dissolved in 20 ml dry tetrahydrofuran and cooled to −78 C. 1.10 eq. of 1 N lithium aluminum hydride in tetrahydrofuran was added slowly. The reaction was stirred at 0 C for 2 hours. The reaction was cooled to −78 C again and quenched with 1 N HCl and extracted with EtOAc three times. The organic was combined, dried over sodium sulfate and concentrated. The residue was purified by column chromatography using 0-100% gradient of EtOAc and hexanes to give 1-(3,4-dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea.

Workup

  1. temperaturecooled to −78 C
  2. temperatureThe reaction was cooled to −78 C again
  3. customquenched with 1 N HCl
  4. extractionextracted with EtOAc three times
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ce459471c0b043b78acec9a89d33a8d0
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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