Carbamic acid, ethyl ester → 2-(3-ethoxycarbonyl-N-methyl-3-aza-propanamido)-5-chlorobenzophenone hydrochloride

HRID 616762

Reaction equation

HRID 616762 reaction equation
[CH3:1][N:2]([C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:3](=[O:6])[CH2:4]Br.C(N(CC)CC)C.[NH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1(C)C(C)=CC=CC=1>[ClH:21].[CH2:33]([O:32][C:30]([NH:29][CH2:4][C:3]([N:2]([C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[CH3:1])=[O:6])=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 8471TriethylamineHCID 76099N-(2-benzoyl-4-chlorophenyl)-2-bromo-N-methylacetamide

Product 1

HCID 706287682-(3-ethoxycarbonyl-N-methyl-3-aza-propanamido)-5-chlorobenzophenone hydrochlorideYield 158.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7.3 g of 2-(N-methyl-bromoacetamido)-5-chlorobenzophenone are heated in 200 ml of anhydrous xylene with 2.2 g of triethylamine and 2 g of urethane (NH2COOC2H5) for 12 hours under reflux whilst stirring. The triethylamine hydrobromide which has precipitated is filtered off with suction after cooling, the filtrate is extracted by shaking with three times 250 ml of water and the organic phase is dried over potassium carbonate, filtered and evaporated in vacuo. The oily residue is dissolved in 400 ml of anhydrous diethyl ether and filtered and 6.5 g of 2-(3-ethoxycarbonyl-N-methyl-3-aza-propanamido)-5-chlorobenzophenone hydrochloride (79% of theory), with a melting point of 156°-158°, are obtained by passing dry hydrogen chloride gas into the ethereal solution.

Workup

  1. temperatureunder reflux
  2. customThe triethylamine hydrobromide which has precipitated
  3. filtrationis filtered off with suction
  4. temperatureafter cooling
  5. extractionthe filtrate is extracted
  6. stirringby shaking with three times 250 ml of water
  7. dry with materialthe organic phase is dried over potassium carbonate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe oily residue is dissolved in 400 ml of anhydrous diethyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-6c8e637e7eac4613b994871ae2ec23ad
Source dataset
uspto-grants-1978_02
Patent number
US04075409

Linked notes

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