Diethyl Ether → HCID 68980202, compound

HRID 1820867Notes

Reaction equation

HRID 1820867 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C=O)C.O>[N+:12]([C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([CH2:2][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[O:4][C:5]=2[CH:11]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 27641902-(chloromethyl)-6-nitro-1,3-benzoxazole

Product 1

HCID 68980202HCID 68980202, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture of 3.00 g (14.1 mmol) of 2-chloromethyl-6-nitrobenzoxazole (VIII.1.a), 1.50 mL (18.0 mmol) of pyrrolidine, and 3.90 g (28.2 mmol) of potassium carbonate in 30 mL of DMF is stirred for 12 hours at 50° C. After this time, the mixture is diluted with water and covered with diethyl ether. The precipitate formed is filtered off and dried at 80° C. Yield: 1.80 g (52% of theory); C12H13N3O3; EII mass spectrum: m/z=248 [M+H]+.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. customdried at 80° C

Sources & evidence

ORD record
ord-454940330c804136ac7cdec137e0624f
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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