Benzenesulfonyl chloride → HCID 68296414, compound

HRID 631873Notes

Reaction equation

HRID 631873 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[NH2:15])=[O:4].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[NH:15][S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23])=[O:4]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 11521576HCID 11521576, compound2×

Product 1

HCID 68296414HCID 68296414, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (Intermediate 5, 1.5 g) in pyridine (20 mL) was added benzenesulfonyl chloride (0.95 mL). The mixture was stirred for 1 hour then concentrated under vacuum. The residue was dissolved in ethyl acetate and washed with 1N hydrochloric acid, dried with magnesium sulfate and filtered. The filtrate was evaporated under vacuum to give the title compound as an off-white crystalline solid (2.4 g).

Workup

  1. concentrationthen concentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N hydrochloric acid
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-48cb155985cd49dc9c4d21d645420729
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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