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Triethylamine → HCID 57962389, compound

HRID 541806
Notes
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Reaction equation

HRID 541806 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[N+:24]([C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)([O-:26])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[N+:24]([C:27]1[CH:28]=[C:29]([S:33]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:6]=[CH:7][CH:8]=2)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)([O-:26])=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 27564813-(Aminomethyl)-1-N-Boc-aniline

Product 1

HCID 57962389HCID 57962389, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a stirring solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (2.00 g, 9.0 mmol) and triethylamine (1.32 mL, 9.45 mmol) in dry tetrahydrofuran (25.5 mL) at 0° C. was slowly added a solution of m-nitrobenzenesulfonyl chloride (2.09 g, 9.45 mmol) in tetrahydrofuran (7.3 mL). The resulting mixture was slowly warmed up to rt and stirred for one additional hour at rt. The reaction mixture was treated with Na2CO3 (aq) and layers separated. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as an off-white powder (4.0 g, 100%). LCMS for C18H21N3O6S (M-Boc+H)+: m/z=308.0. 1H NMR (400 MHz, CD3OD): δ 8.43 (t, J=2.0 Hz, 1H), 8.31 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.04 (dt, J=8.0, 2.8 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.19 (br, 1H), 7.04 (m, 2H), 6.77 (dt, J=7.2, 1.2 Hz, 1H), 4.13 (s, 2H).

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b72ca2893ee43e99ce6a3c319442f81
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871753B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes