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

HRID 549677Notes

Reaction equation

HRID 549677 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-334c2825f4754946b09b3c26da2248c6
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

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