2-Ethylbutyraldehyde → HCID 22603058, compound

HRID 1019072Notes

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

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-ethylpropyl)benzenemethanol (interm 28).

Workup

customThe following reaction
stirringThe mixture was stirred for one hour
temperatureto warm to RT overnight
stirringthe mixture was stirred for 15 minutes
extractionThe separated aqueous phase was extracted with EtOAc (1000 ml)
customThe separated organic layer was dried
filtrationfiltered
customthe solvent evaporated
customThe residue was crystallized from methyl isobutyl keton
filtrationThe precipitate was filtered off
customdried

Sources & evidence

ORD record: ord-24e532ab46d2413481edb5baab8198c3
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486187B1

Reaction notes

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