HCID 70565949, compound → HCID 20288317, compound

HRID 126924Notes

Reaction equation

HRID 126924 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[C@H:13]([OH:14])[CH2:12][N:11]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:10]2)=O)=[CH:4][CH:3]=1>S(Cl)(Cl)(=O)=O>[ClH:1].[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[O:14][C:13]3[CH2:12][N:11]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[CH2:10][C:9]=3[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 70565949HCID 70565949, compound

Product 1

HCID 20288317HCID 20288317, compound

Reagents, catalysts & solvents 1

HCID 24648Sulfuryl chlorideSolvent

Procedure

Two grams of trans-4-chloro-N-(1-cyclohexyl-4-hydroxy-3-pyrrolidinyl)benzamide was dissolved in 50 ml of cold (0° C.) sulfonyl chloride; the solution was allowed to warm to room temperature and stirred overnight. Excess sulfonyl chloride was removed at 50° C./60 mm. Fifty milliliters of carbon tetrachloride was added to the residue and then evaporated under vacuum. When acetone was added to the residue, it crystallized to a white solid (quantitative yield). Recrystallization from absolute ethanol gave product, m.p. 303°-304° C.

Workup

  1. customExcess sulfonyl chloride was removed at 50° C./60 mm
  2. additionFifty milliliters of carbon tetrachloride was added to the residue
  3. customevaporated under vacuum
  4. additionWhen acetone was added to the residue, it

Sources & evidence

ORD record
ord-77f7a7b0ef654b508bb026ec1e7951ed
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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