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Tetrahydrofuran → N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-carboxamide

HRID 264859
Notes
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Reaction equation

HRID 264859 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH2:23][F:24])([CH2:21][F:22])[CH:9]=1)=[O:7])#[N:2].[BH4-].[Na+].O1CCCC1>CO>[C:1]([CH2:3][CH2:4][NH:5][C:6]([CH:8]1[C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH2:23][F:24])([CH2:21][F:22])[CH2:9]1)=[O:7])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10735656N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxamide

Product 1

HCID 19037047N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-carboxamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A mixture of 0.33 g of N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxamide, 0.20 g of sodium borohydride, 20 ml of tetrahydrofuran and 10 ml of methyl alcohol was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and 2N hydrochloric acid was added therein. The resultant mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (developing solution, ethyl acetate:hexane=1.1) to obtain 0.17 g of N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-3,4-dihydro-6-nitro-2H-1-benzopyran-4-carboxamide with a melting point of 137°-138° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 2N hydrochloric acid
  2. additionwas added
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2f4e1248ebf40d09b3dcea1eb50534d
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05646308

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes