Dichloromethane → HCID 54234994, compound

HRID 1578400Notes

Reaction equation

HRID 1578400 reaction equation
[CH2:1]([NH:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:2].C(Cl)Cl.[C:24]([C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([OH:36])=O)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(N(CC)CC)C>[C:24]([C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([N:3]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:1][CH3:2])=[O:36])(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68132-Benzoylbenzoic AcidHCID 54287253HCID 54287253, compound

Product 1

HCID 54234994HCID 54234994, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Twenty-four grams of trans N-(2-ETHYLAMINOCYCLOHEXYL)-p-TOLUENESULFONAMIDE from Example III,200 ml of methylenechloride, 24ml of triethylamine and 20 grams of ψ-acid chloride of o-benzoylbenzoic acid were mixed together and refluxed 4 hours. The mixture was extracted successively with water, 15% hydrochloric acid, and saturated sodium carbonate solution. The methylenechloride solution was dried over magnesium sulfate, then evaporated to dryness. The residue was slurried with ethyl acetate and filtered. Recrystallization from ethyl acetate afforded trans-2-BENZOYL-N-[2-(p-TOLUENESULFONAMIDO)CYCLOHEXYL]-N-ETHYL BENZAMIDE, mp. 201.5°-204°C.

Workup

  1. temperaturerefluxed 4 hours
  2. extractionThe mixture was extracted successively with water, 15% hydrochloric acid, and saturated sodium carbonate solution
  3. dry with materialThe methylenechloride solution was dried over magnesium sulfate
  4. customevaporated to dryness
  5. filtrationfiltered
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6dbdb8015e7d49b2b954a08528ee5c9d
Source dataset
uspto-grants-1976_02
Patent number
US03936471

Reaction notes

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