2-Chloroethyl isocyanate → {3-[3-(2-Chloro-ethyl)-ureido]-phenyl}-carbamic acid tert-butyl ester

HRID 386468Notes

Reaction equation

HRID 386468 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21]>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:20]([NH:19][CH2:18][CH2:17][Cl:16])=[O:21])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 67229696{3-[3-(2-Chloro-ethyl)-ureido]-phenyl}-carbamic acid tert-butyl esterYield 132.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-Amino-phenyl)-carbamic acid tert-butyl ester (0.5 g, 2.4 mmol) and 1-Chloro-2-isocyanato-ethane (0.25 ml, 2.9 mmol) in dry tetrahydrofuran (20 ml) were stirred at room temperature overnight. Reaction was quenched with water (50 ml) then extracted with dichloromethane (3×50 ml). Combined organics dried (magnesium sulphate) and concentrated in vacuo. The crude residue was purified by column chromatography (eluent 10% ethylacetate in dichloromethane) to afford the title compound (1 g). HPLC retention time 7.45 min. Mass spectrum (ES+) m/z 314 (M+H)

Workup

  1. customReaction
  2. customwas quenched with water (50 ml)
  3. extractionthen extracted with dichloromethane (3×50 ml)
  4. dry with materialCombined organics dried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (eluent 10% ethylacetate in dichloromethane)

Sources & evidence

ORD record
ord-3e51cdcf0f644823ad2a1cb0f00feed1
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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