Triethylamine → Tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamate

HRID 423118Notes

Reaction equation

HRID 423118 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:11][CH2:12][NH:13][C:14](OC2C=CC=CC=2)=[O:15])=[CH:6][CH:5]=1.C([N:33](CC)CC)C>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:11][CH2:12][NH:13][C:14]([NH2:33])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 57750354tert-butyl N-[1-(4-chlorophenyl)-3-(phenoxycarbonylamino)propyl]carbamate2×

Product 1

HCID 57750307Tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ammonium chloride (113 mg, 2.11 mmol) was added in one portion to tert-butyl N-[1-(4-chlorophenyl)-3-(phenoxycarbonylamino)propyl]carbamate (Intermediate 109) (427 mg, 1.05 mmol) and triethylamine (0.882 mL, 6.33 mmol) in DMF (3 mL). The resulting solution was stirred at 0.352 molar for 24 hours. The reaction mixture was concentrated and diluted with EtOAc (20 mL) and washed with water (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamate (346 mg, 100%),

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed with water (20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1dbc59e56a43492c9c74bc2a6ce38c88
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

Loading…