Diethyl Ether → HCID 53697817, compound

HRID 597747Notes

Reaction equation

HRID 597747 reaction equation
[N+:1]([C:4](=[C:8]1[NH:13][CH2:12][CH2:11][CH2:10][S:9]1)[C:5](=[O:7])[CH3:6])([O-:3])=[O:2].[Br:14]N1C(=O)CCC1=O.C(OCC)C>C(Cl)(Cl)(Cl)Cl>[Br:14][N:13]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[C:4]([N+:1]([O-:3])=[O:2])[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 714007471-Nitro-1-(1,3-thiazinan-2-ylidene)propan-2-one

Product 1

HCID 53697817HCID 53697817, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 10.1 g of 2 and 10.0 g of N-bromosuccinimide in 150 ml of carbon tetrachloride was stirred at room temperature for 18 hours. The resulting mixture was filtered and the filtrate stripped of solvent under reduced pressure to leave a slightly gummy yellow solid. The solid was treated with ethyl ether and the remaining solid collected (bright yellow solid, m.p.: 101°-104°), then dissolved in methylene chloride. The solution was treated with Norite, filtered and the solvent stripped under reduced pressure to leave a solid which on recrystallization from ethyl acetate gave 12 as a yellow solid, m.p.: 105°-109°.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto leave a slightly gummy yellow solid
  3. customthe remaining solid collected (bright yellow solid, m.p.: 101°-104°)
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated with Norite
  6. filtrationfiltered
  7. customto leave a solid which
  8. customon recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-41affeba32f0493a825aaa503824ba03
Source dataset
uspto-grants-1977_03
Patent number
US04015001

Reaction notes

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