Diethyl Ether → HCID 20442929, compound

HRID 1164533Notes

Reaction equation

HRID 1164533 reaction equation
[CH3:1][NH:2][C:3]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:6].[Br:19][CH2:20][C:21](Br)=[O:22].C(OCC)C>C(OCC)(=O)C>[CH3:1][N:2]([C:21](=[O:22])[CH2:20][Br:19])[C:3]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:4]=1[C:5](=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21833Benzophenone, 2',5-dichloro-2-methylamino-HCID 61147Bromoacetyl bromide

Product 1

HCID 20442929HCID 20442929, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 56 g of 2-methylamino-2', 5-dichlorobenzophenone in 400 cc of ethyl acetate there are added an equal volume of ice and then 23 cc of bromoacetylbromide. After stirring overnight at room temperature, 300 cc of ethyl ether are added. The solvent layer is decanted, washed with 2 N caustic soda, and then washed with water until neutral. It is then dried over sodium sulfate, filtered, and evaporated to dryness. The residue is treated with petroleum ether and then recrystallized from ethyl acetate. In this way there are obtained 65 g of crystals; yield: 81%.

Workup

  1. customThe solvent layer is decanted
  2. washwashed with 2 N caustic soda
  3. washwashed with water until neutral
  4. dry with materialIt is then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionThe residue is treated with petroleum ether
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6d025385589444579e3fb540965d5824
Source dataset
uspto-grants-1983_01
Patent number
US04370347

Reaction notes

Loading…