Tetrahydrofuran → HCID 68687333, compound

HRID 1991425Notes

Reaction equation

HRID 1991425 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][C:6]=1[CH2:7][NH2:8])([O-])=O.CC[N:16]([CH:20](C)C)C(C)C.[NH4+].[Cl-].C1C[O:28][CH2:27]C1>CO.[Zn]>[O:28]=[C:27]1[NH:8][CH2:7][C:6]2[C:5](=[CH:12][C:11]([C:20]#[N:16])=[CH:10][CH:9]=2)[NH:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 12423134HCID 12423134, compound

Product 1

HCID 68687333HCID 68687333, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

24 mmol of 2-Nitro-4-chloro-benzylamine hydrochloride were dissolved in THF. 2.2 eq of DIPEA were added and the reaction mixture cooled to 0° C. 3.5 eq. of ethyl chloroforamte were added dropwise and the reaction stirred for 15 min. After extraction from ethylacetate/sat. NaHCO3 and evaporation of the organic layer a light brown solid resulted. This was taken up in MeOH/sat. NH4Cl (1:1). 6 g of Zn was added and the suspension stirred at rt for 4 h. The solid was filtered off, the methanol reduced and the product isolated via extraction with ethylacetate. After evaporation a light yellow solid resulted. MS(ISO): 174.2 (MH+)

Workup

  1. addition3.5 eq. of ethyl chloroforamte were added dropwise
  2. extractionAfter extraction from ethylacetate/
  3. customNaHCO3 and evaporation of the organic layer a light brown solid
  4. customresulted
  5. stirringthe suspension stirred at rt for 4 h
  6. filtrationThe solid was filtered off
  7. customthe product isolated via extraction with ethylacetate
  8. customAfter evaporation a light yellow solid
  9. customresulted

Sources & evidence

ORD record
ord-48bf433def35407dbe8f68fdb170039f
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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