Cyclohexanol → HCID 15956113, compound

HRID 1474005Notes

Reaction equation

HRID 1474005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[OH:14].[CH:15]1(O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[CH:22]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[O:14][CH2:22][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 15956113HCID 15956113, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure general for O-alkylation, Method C, 2-chloro-5-(thiazol-2-ylamino)phenol (70 mg, 0.31 mmol), 1-cyclohexanol (34 μM, 0.32 mmol), Ph3P (84 mg, 0.32 mmol) were suspended in THF (0.1 mL). The reaction flask was lowered into a sonication bath and sonicated for several minutes giving a clear and highly viscous solution. While sonication, DEAD (0.063 mL, 0.32 mmol) was added slowly. The reaction mixture was stirred for 1 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 5% yield (5 mg).

Workup

  1. customThe reaction flask was lowered into a sonication bath
  2. customsonicated for several minutes
  3. customgiving a clear and highly viscous solution
  4. additionwas added slowly

Sources & evidence

ORD record
ord-f44d642e5acc4774b4662965dc765cd7
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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