Diisopropyl Ether → 5-Nitro-2-pyrrolidin-1-ylmethylbenzoxazole

HRID 735100

Reaction equation

HRID 735100 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[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(OC(C)C)(C)C>CN(C=O)C.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([CH2:2][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:7][C:6]=2[CH:8]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 27641892-(Chloromethyl)-5-nitro-1,3-benzoxazole

Product 1

HCID 597669925-Nitro-2-pyrrolidin-1-ylmethylbenzoxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture of 3 g (14.11 mmol) of 2-chloromethyl-5-nitrobenzoxazole, 1.5 mL (17.97 mmol) of pyrrolidine, and 3.9 g (28.22 mmol) of potassium carbonate in 30 mL of DMF is stirred for 4 hours at 50° C. Then the reaction mixture is diluted with water and covered with diisopropyl ether, The precipitated yellow solid is suction filtered, washed again, and dried in the circulating air dryer at 60° C. Yield: 1.8 g (52% of theory); C12H13N3O3 (M=247.25); calc.: molecular ion peak (M+H)+: 248; found: molecular ion peak (M+H)+: 248; Rf value: 0.4 (silica gel, dichloromethane/ethanol (20:1)).

Workup

  1. filtrationfiltered
  2. washwashed again
  3. customdried in the circulating air dryer at 60° C

Sources & evidence

ORD record
ord-652e8ce8327f40859f9e5f8de2b56507
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Linked notes

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