Isopropanol → 2-Chloro-6-(propan-2-yloxy)-1,3-benzothiazole

HRID 70140Notes

Reaction equation

HRID 70140 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:12](O)([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 147498432-Chlorobenzo[d]thiazol-6-ol

Product 1

HCID 219858112-Chloro-6-(propan-2-yloxy)-1,3-benzothiazoleYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chlorobenzo[d]thiazol-6-ol (0.800 g, 4.31 mmol), isopropanol (0.36 mL, 4.74 mmol) and triphenylphosphine (1.24 g, 4.74 mmol) were mixed in THF (1.4 mL) and sonicated. DIAD (0.933 mL, 4.74 mmol) was added dropwise over ˜2 min. After 1 h, the reaction mixture was concentrated under reduced pressure. The material was purified by column chromatography (0 to 10% EtOAc in Hexanes gradient), yielding 0.894 g (91%) of the title compound as a light brown oil. LC-MS: RT=10.21 min., [M+H]+=228.0. Rf=0.50 in 10% EtOAc/Hexanes.

Workup

  1. customsonicated
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe material was purified by column chromatography (0 to 10% EtOAc in Hexanes gradient)

Sources & evidence

ORD record
ord-9290c10a6ed741bcb9413191ca7e802c
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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