Benzenesulfonyl chloride → HCID 59977570, compound

HRID 2271089Notes

Reaction equation

HRID 2271089 reaction equation
[NH2:1][C@@H:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C@H:3]1[OH:13].C(N(CC)CC)C.[CH:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[C:24]1([S:27]([NH:1][C@@H:2]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][CH2:5][CH2:4][C@H:3]2[OH:13])(=[O:29])=[O:28])[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13125682HCID 13125682, compound

Product 1

HCID 59977570HCID 59977570, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of trans-5-amino-6,7,8,9-tetrahydro-5H-benzocyclo hepten-6-ol (0.056 g, 0.32 mmol; example 15 a) in methylene chloride (10 ml) and triethylamine (1 ml) was added 4-benzene sulfonyl chloride (0.056 g, 0.32 mmol). The reaction mixture was stirred at 0° C. then allowed to come to room temperature for 72 hours. The reaction mixture was diluted with methylene chloride, then washed with 10% hydrochloric acid, saturated potassium hydrogen carbonate solution, dried over MgSO4, filtered and evaporated. Recrystallization from ethyl acetate/n-heptane yielded trans-5-(N-phenylsulfonylamino)-6,7,8,9-tetrahydro-5H-benzocyclo hepten-6-ol as white crystals (0.071 g, 71% yield), m.p. 128.0-128.2° C.

Workup

  1. washwashed with 10% hydrochloric acid, saturated potassium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customRecrystallization from ethyl acetate/n-heptane

Sources & evidence

ORD record
ord-98c22b1501f0441babb47881292be546
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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