Dimethylformamide → HCID 69476616, compound

HRID 1271399Notes

Reaction equation

HRID 1271399 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.CN(C)C=O.[H-].[Na+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH:31]=[CH:32][C:33]2[CH:43]=[CH:42][C:36]3[O:37][C:38]([F:41])([F:40])[O:39][C:35]=3[CH:34]=2)[O:29][CH:30]=1>O>[F:41][C:38]1([F:40])[O:37][C:36]2[CH:42]=[CH:43][C:33]([CH:32]=[CH:31][C:28]3[O:29][CH:30]=[C:26]([CH2:25][O:16][C:13]4[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]5[CH:5]=[CH:4][N:3]=[N:2]5)=[CH:15][CH:14]=4)[N:27]=3)=[CH:34][C:35]=2[O:39]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 69292417HCID 69292417, compound

Product 1

HCID 69476616HCID 69476616, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.217 g (1.00 mmol) 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenol in 4 ml N,N-dimethyl formamide 40 mg (1.00 mmol) of NaH (60% dispersion in mineral oil) were added and the mixture stirred for 15 min at room temperature. Subsequently 0.3 g (1.00 mmol) 4-chloromethyl-2-[2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-vinyl]-oxazole were added and stirring continued for 12 h. 20 ml of water were added, the resulting precipitate collected, washed with water (2×), methanol/water (1:1), ether (3×) and dried in vacuo yielding 0.42 g (87%) 1-[4-(4-{2-[2-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 12 h
  3. customthe resulting precipitate collected
  4. washwashed with water (2×), methanol/water (1:1), ether (3×)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-23414c473c5d448db62280bfdd21aefb
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

Loading…