Benzoyl chloride → HCID 178473102, compound

HRID 1654532Notes

Reaction equation

HRID 1654532 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16][CH2:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:34]([N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16][CH2:15]1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178473103HCID 178473103, compound

Product 1

HCID 178473102HCID 178473102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold mixture of 4.0 g. (10 mMol) ethyl trans-4-[2-(4-chlorobenzenesulphonylamino)-ethyl]-cyclohexyloxyacetate, 50 ml. methylene chloride and 1.5 g. (15 mMol) triethylamine is added dropwise a mixture of 1.4 g. (10 mMol) benzoyl chloride and 30 ml. methylene chloride. The reaction mixture is maintained for 4 hours at reflux temperature, cooled, filtered and the filtrate washed with dilute hydrochloric acid and water. It is then dried with anhydrous sodium sulphate and evaporated After purification over silica gel/ cyclohexane/diethyl ether (2:1 v/v), there is obtained a yield of 1.7 g (67% of theory); m.p. 81°-82° C.

Workup

  1. additiona mixture of 1.4 g
  2. temperatureThe reaction mixture is maintained for 4 hours
  3. temperatureat reflux temperature
  4. temperaturecooled
  5. filtrationfiltered
  6. washthe filtrate washed with dilute hydrochloric acid and water
  7. dry with materialIt is then dried with anhydrous sodium sulphate
  8. customevaporated
  9. customAfter purification over silica gel/ cyclohexane/diethyl ether (2:1 v/v)
  10. customthere is obtained a yield of 1.7 g (67% of theory)

Sources & evidence

ORD record
ord-2b0432629a5f43768151d3ab04c20917
Source dataset
uspto-grants-1995_04
Patent number
US05407951

Reaction notes

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