2-(Dimethylamino)ethanol → 2-[2-(1,3-benzothiazol-2-yl)-5-nitrophenoxy]-N,N-dimethylethanamine

HRID 339498Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[S:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[O:1][CH2:42][CH2:41][N:40]([CH3:44])[CH3:39]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of 2-(2-hydroxy-4-nitrophenyl)benzothiazole (0.15 g, 0.55 mmol), triphenylphosphine (0.216 g, 0.825 mmol) and N,N-dimethylethanolamine (0.059 g, 0.66 mmol) in dry THF (10 ml) at 0° C. was added dropwise DIAD (0.167 g, 0.825 mmol). The reaction mixture was stirred at 0° C. for 0.5 h, then left to rise to room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (20:1 DCM/MeOH) to give the title compound (0.089 g, 47%) as a yellow solid.

Workup

waitleft
waitto rise to room temperature overnight
customThe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography (20:1 DCM/MeOH)

Sources & evidence

ORD record: ord-99059d2f655c49faabc6de36e74bc76c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895313B2

Reaction notes

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