Nitrofungin → HCID 13101307, compound

HRID 2295972Notes

Reaction equation

HRID 2295972 reaction equation
CC1(C=CCC)C(C)=CC=C(S([O-])(=O)=O)C1.[CH3:17][C:18](=[CH2:22])[CH2:19][CH2:20][OH:21].[Na].[Cl:24][C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1O>CN(C)C=O>[Cl:24][C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[O:21][CH2:20][CH2:19][C:18]([CH3:17])=[CH2:22]

Participants

6

Reactant 4

HCID 12074NitrofunginHCID 129883-Methyl-3-buten-1-olHCID 5360545SodiumHCID 86739187HCID 86739187, compound

Product 1

HCID 13101307HCID 13101307, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-3-butenyltosylate derived from 12.9 g of 3-methyl-3-buten-1-ol by a conventional procedure was reacted with 31 g of sodium salt of 2-chloro-4-nitrophenol in 250 ml of dimethylformamide. The resultant mixture was stirred at 90°-100° C. for 2.5 hours and then poured into ice-water, followed by extraction with benzene. The solvent was removed under reduced pressure, and the precipitated crystals were subjected to filtration by a glass filter and washed with ether to give 29.3 g of 3-chloro-4-(3-methyl-3-butenyloxy)nitrobenzene. M.P. 38°-39° C.

Workup

  1. extractionfollowed by extraction with benzene
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe precipitated crystals were subjected to filtration by a glass
  4. filtrationfilter
  5. washwashed with ether

Sources & evidence

ORD record
ord-bef11243f09f4125977ab40566c522df
Source dataset
uspto-grants-1984_01
Patent number
US04427596

Reaction notes

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