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Trifluoroacetic acid → 5-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 54756
Notes
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Reaction equation

HRID 54756 reaction equation
[O-:1][C:2]#[N:3].[Na+].FC(F)(F)C(O)=O.[NH2:12][CH2:13][CH2:14][O:15][CH:16]1[C:22]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=2[N:20]([C:28](=[O:47])[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:43])=[CH:31][C:30]=2[O:45][CH3:46])[CH2:19][CH2:18][CH2:17]1.C(=O)([O-])O.[Na+]>CN(C)C=O.CCCCCC>[NH:12]([CH2:13][CH2:14][O:15][CH:16]1[C:22]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=2[N:20]([C:28](=[O:47])[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:43])=[CH:31][C:30]=2[O:45][CH3:46])[CH2:19][CH2:18][CH2:17]1)[C:2]([NH2:3])=[O:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 189171925-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine
Yield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

0.12 g of sodium cyanate and 0.22 ml of trifluoro-acetic acid were added to a solution of 0.5 g of 5-(2-amino-ethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine dissolved in 15 ml of dry dimethylformamide. The mixture was stirred at 80° C. for 1 hour. After cooling, the reaction mixture was mixed with slight amounts of a saturated aqueous sodium hydrogen-carbonate solution and hexane, followed by extraction with ethyl acetate. The organic layer was water-washed, then dried over magnesium sulfate and subjected to vacuum distillation to remove the solvent. The resiude was recrystallized from acetone-n-hexane to obtain 0.41 g (76%) of 5-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashed
  4. dry with materialdried over magnesium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. customThe resiude was recrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-867fbd1a798e4394826c60b2e54d6ee1
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05622947

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes