Triphenylphosphine → N-(4-Chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)thiazol-2-amine

HRID 1474002Notes

Reaction equation

HRID 1474002 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].[CH3:15][C:16]([CH3:21])=[CH:17][CH:18](O)[CH3:19].C1C=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][CH:18]([CH:17]=[C:16]([CH3:21])[CH3:15])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1381904-Methylpent-3-en-2-olHCID 5462977Diethyl azodicarboxylateHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 86645046N-(4-Chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)thiazol-2-amineYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure general for O-alkylation, Method C, 2-chloro-5-(thiazol-2-ylamino)phenol (50 mg, 0.22 mmol), 4-Methylpent-3-en-2-ol (23 mg, 0.23 mmol), Ph3P (58 mg, 0.22 mmol) were suspended in THF (0.07 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 (0.043 mL, 0.22 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 4/1) in 24% yield (16 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-80fa23504fce4b51832a162d9aef935f
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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