O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 2042823Notes

Reaction equation

HRID 2042823 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]([F:32])([F:31])[C:25]1([C:28](O)=[O:29])[CH2:27][CH2:26]1.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][C:35]=1[N+:42]([O-:44])=[O:43]>C1COCC1>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH:39][C:28]([C:25]2([C:24]([F:32])([F:31])[F:23])[CH2:27][CH2:26]2)=[O:29])=[CH:36][C:35]=1[N+:42]([O-:44])=[O:43]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 18796740(4-Chloro-3-nitrophenyl)methanamine

Product 1

HCID 59529820N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBTU (0.44 g, 1.4 mmol) and TEA (0.43 mL, 3.1 mmol) are added to 1-trifluoromethyl-cyclopropanecarboxylic acid (0.19 g, 1.2 mmol) in THF (5 mL). After 10 min at rt 4-chloro-3-nitro-benzylamine (0.23 g, 1.2 mmol) is added to the reaction mixture and stirring is continued overnight. The mixture is concentrated, the crude is diluted with EtOAc and washed with sat.aq. NaHCO3-solution, water and brine. The organic layer is dried with Na2SO4 and concentrated.

Workup

  1. concentrationThe mixture is concentrated
  2. additionthe crude is diluted with EtOAc
  3. washwashed with sat.aq
  4. dry with materialThe organic layer is dried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea9ada327f6d4ad18c1661318e265f51
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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