2-Ethylbutyraldehyde → HCID 22603058, compound

HRID 2307871Notes

Reaction equation

HRID 2307871 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:23]([CH:25]([CH2:28][CH3:29])[CH:26]=[O:27])[CH3:24].[NH4+].[Cl-]>C1COCC1>[S:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([CH:26]([CH:25]([CH2:28][CH3:29])[CH2:23][CH3:24])[OH:27])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 73592-EthylbutyraldehydeHCID 25517Ammonium ChlorideHCID 234496N-(4-Bromophenyl)benzo[d]thiazol-2-amineHCID 178418339Butyllithium

Product 1

HCID 22603058HCID 22603058, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

The following reaction was performed under a N2 atmosphere. A mixture of N-(4-bromophenyl)-2-benzothiazolamine (0.492 mol) in THF (2700 ml) was stirred at −70° C. Butyllithium (0.984 mol; 2.5 M in hexane) was added dropwise at −65° C. The mixture was stirred for one hour. A solution of 2-ethyl-butanal (0.492 mol) in THF (300 ml) was added dropwise at −75° C. The mixture was allowed to warm to RT overnight. A 10% aqueous NH4Cl solution (3000 ml) was added and the mixture was stirred for 15 minutes The separated aqueous phase was extracted with EtOAc (1000 ml). The separated organic layer was dried, filtered and the solvent evaporated. The residue was crystallized from methyl isobutyl keton. The precipitate was filtered off and dried, yielding 109 g (68%) of (±)-4-(2-benzothiazolylamino)-α-(1-ethyl-propyl)benzenemethanol (interm 28).

Workup

  1. customThe following reaction
  2. stirringThe mixture was stirred for one hour
  3. temperatureto warm to RT overnight
  4. stirringthe mixture was stirred for 15 minutes The separated aqueous phase
  5. extractionwas extracted with EtOAc (1000 ml)
  6. customThe separated organic layer was dried
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was crystallized from methyl isobutyl keton
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-057831b3e181465c8135b6ea1ec43399
Source dataset
uspto-grants-2004_12
Patent number
US06833375B2

Reaction notes

Loading…