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Benzenesulfonyl chloride → Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl ester

HRID 1061207
Notes
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Reaction equation

HRID 1061207 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)(=O)C.N1C=CC=CC=1>[C:25]1([S:31]([NH:1][C:2]2[CH:3]=[C:4]([O:16][C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:5]=[CH:6][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 86584542Benzoic acid 3-amino-4-benzyloxy-phenyl ester

Product 1

HCID 86584543Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl esterYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of benzoic acid 3-amino-4-benzyloxy-phenyl ester (5.91 g, 18.5 mmol) (which was obtained in Example 16) in ethyl acetate (100 mL) and pyridine (20 mL) at 0° C. was added dropwise phenyl sulfonyl chloride (3.26 g, 18.5 mmol) in 50 mL of ethyl acetate. After one hour at 0° C. the mixture was warmed to room temperature and stirred at room temperature over night. The reaction mixture was washed with water and the organic layer was dried (MgSO4) and concentrated. Recrystallization from CH2Cl2/hexanes gave the title compound as a white solid (4.65 g, 61%); 1H NMR (300 MHz, CDCl3) δ 4.93 (s, 2H), 6.90-7.80 (m, 15H), 8.12 (d, J=8.5 Hz, 2H), 9.81 (s, 1H); MS (ES) m/z: 458.9 (MH+, 100%); HRMS Calcd. for C26H22NO5S(MH+): 459.1141. Found: 459.1151.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customRecrystallization from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-e7bf61a3db0d440ca99fd6d0c1c2580b
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06525202B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes