4-Nitrophenyl morpholin-4-ylcarbamate → HCID 23513714, compound

HRID 507740Notes

Reaction equation

HRID 507740 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[CH:5]([C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][Cl:22])=[CH:15][CH:14]=1)[C:6]2=[O:11].[N+](C1C=CC([O:34][C:35](=O)[NH:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=CC=1)([O-])=O>CC#N.CN(C)C1C=CN=CC=1>[Cl:22][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:5]2[C:4](=[O:24])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[NH:1][C:35]([NH:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[O:34])[C:6]2=[O:11])=[O:23])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 207362844-Nitrophenyl morpholin-4-ylcarbamateHCID 23513707HCID 23513707, compound

Product 1

HCID 23513714HCID 23513714, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-amino-2-[4-(2-chloroethoxy)benzoyl]indan-1,3-dione (36 g, 105 mmol) in CH3CN (600 mL) was added morpholin-4-ylcarbamic acid 4-nitrophenyl ester (40 g, 120 mmol) followed by 4-dimethylaminopyridine (640 mg, 5.2 mmol). The reaction was heated at reflux for 4 hours then cooled to room temp. and stirred overnight. The bright yellow solid is collected by filtration, rinsed with Et2O and dried under vacuum to give the desired semicarbazide (40.5 g, 82% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 hours
  3. temperaturethen cooled to room temp.
  4. filtrationThe bright yellow solid is collected by filtration
  5. washrinsed with Et2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7bf2586cee63466da95120b1f806597e
Source dataset
uspto-grants-2010_08
Patent number
US07786112B2

Reaction notes

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