Dichloromethane → HCID 21528418, compound

HRID 1658643Notes

Reaction equation

HRID 1658643 reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C(Cl)Cl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(N(CC)CC)C>[CH3:23][S:24]([O:1][CH2:2][C:3]#[C:4][CH:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 21528383HCID 21528383, compound

Product 1

HCID 21528418HCID 21528418, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This preparation illustrates methods according to step 3 of the process for preparing the compounds of formula A. In this preparation a solution containing 0.25 g. of 5-(3-hydroxy-prop-1-ynyl)-5H-dibenzo[a,d]cycloheptene in 25 ml. of anhydrous methylene chloride containing 0.25 ml. of triethylamine is stirred and cooled to maintain the temperature between 0°C and -10°C and 0.15 ml. of methanesulfonyl chloride is added. Cooling is then discontinued and the temperature of the mixture allowed to rise, with stirring, for 15 minutes. The solution is then poured into ice water, resulting in a two-phase organic-aqueous mixture. The organic layer is separated and washed successively with ice cold 1Normal aqueous hydrochloric acid, water, and saturated brine, and then dried over sodium sulfate and evaporated under vacuum yielding 5-(3-methanesulfonyloxyprop-1-ynyl)-5H-dibenzo[a,d] cycloheptene which is of sufficient purity to be used directly as starting material for subsequent examples.

Workup

  1. customaccording to step 3 of the process for preparing the compounds of formula A
  2. customIn this preparation a solution
  3. additioncontaining 0.25 g
  4. temperaturecooled
  5. temperatureto maintain the temperature between 0°C and -10°C and 0.15 ml
  6. temperatureCooling
  7. customresulting in a two-phase organic-aqueous mixture
  8. customThe organic layer is separated
  9. washwashed successively with ice cold 1Normal aqueous hydrochloric acid, water, and saturated brine
  10. dry with materialdried over sodium sulfate
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-02a4bb1c1d2b4fbb85a4e6eb3b8522d7
Source dataset
uspto-grants-1976_06
Patent number
US03965181

Reaction notes

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