p-Bromobenzenesulfonyl chloride → tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamate

HRID 423556Notes

Reaction equation

HRID 423556 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 7213233tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromobenzenesulfonyl chloride (256 mg, 1 mmol) was added dropwise to a solution of 1,1-dimethylethyl (2-aminoethyl)carbamate (197 mg, 1 mmol) and triethylamine (0.42 mL, 3 mmol) in CH2Cl2 (5 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was then concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 362 mg (96%) of 1,1-dimethylethyl (2-{[(4-bromophenyl)sulfonyl]amino}ethyl)carbamate as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.68 (m, 2H), 7.67-7.61 (m, 2H), 5.28 (bs, 1H), 4.78 (bs, 1H), 3.26-3.20 (m, 2H), 3.11-3.03 (m, 2H), 1.43 (s, 9H); LRMS (ESI), m/z 379/381 (M+H).

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2a628b11de5c47c19f23f8e884560813
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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