Triethylamine → HCID 58812957, compound

HRID 1962302Notes

Reaction equation

HRID 1962302 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.Cl>[CH:25]([S:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=1)(=[O:28])=[O:27])=[CH2:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 58812957HCID 58812957, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-aminophenylcarbamate (2.63 g, 12.63 mmol) and triethylamine (7.04 mL, 50.51 mmol) were combined in dichloromethane (50 mL) and cooled in an ice bath. After drop wise addition of 2-chloroethanesulfonyl chloride (1.45 mL, 13.9 mmol), the solution was stirred at ambient temperature for 4 h then diluted with 0.5M HCl and extracted into dichloromethane. The product was purified by column chromatography on silica gel, eluting with 1% methanol/dichloromethane to give 2.48 g (66%).

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted into dichloromethane
  3. customThe product was purified by column chromatography on silica gel
  4. washeluting with 1% methanol/dichloromethane
  5. customto give 2.48 g (66%)

Sources & evidence

ORD record
ord-3c57f85f00474ac4a16244295642fba6
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Reaction notes

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