3,4-Bis(benzyloxy)-5-nitrobenzoic acid → [(Z)-[amino-[2-(trifluoromethyl)-3-pyridinyl]methylidene]amino] 3-nitro-4,5-bis(phenylmethoxy)benzoate

HRID 62021Notes

Reaction equation

HRID 62021 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O/[N:30]=[C:31](\[NH2:42])/[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38]([F:41])([F:40])[F:39]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:12]([O:14]/[N:30]=[C:31](\[NH2:42])/[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38]([F:41])([F:39])[F:40])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 462019253,4-Bis(benzyloxy)-5-nitrobenzoic acidHCID 83401048HCID 83401048, compound

Product 1

HCID 87544316[(Z)-[amino-[2-(trifluoromethyl)-3-pyridinyl]methylidene]amino] 3-nitro-4,5-bis(phenylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,4-bis(benzyloxy)-5-nitrobenzoic acid (0.759 g, 2 mmol) in dimethylformamide (10 mL) at room temperature was added 1,1-carbonyldiimidazole (0.34 g, 2.10 mmol) in one portion. The resulting yellow mixture was allowed to stir for ninety minutes whereupon (Z)—N′-hydroxy-2-(trifluoromethyl)nicotinimidamide (0.41 g, 2 mmol) was added in one portion. The resulting mixture was stifled at room temperature for two hours and then poured onto water (100 mL). The resulting precipitate was filtered off, washed with water and dried. After recrystallisation from dichloromethane/isopropanol, (Z)—N′-(3,4-bis(benzyloxy)-5-nitrobenzoyloxy)-2-(trifluoromethyl)nicotinimidamide was obtained as a light yellow solid, 0.88 g (78%).

Workup

  1. additionwas added in one portion
  2. additionpoured onto water (100 mL)
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customAfter recrystallisation from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-bfc8d16801ea486c94860d5c14b24560
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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