Ammonia → HCID 13134781, compound

HRID 444324Notes

Reaction equation

HRID 444324 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([OH:19])=O.[NH3:20].O>O1CCCC1.C(Cl)(=O)C(Cl)=O.CN(C)C=O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([NH2:20])=[O:19]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 12443724HCID 12443724, compound

Product 1

HCID 13134781HCID 13134781, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 65578Oxalyl chlorideCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 mg of (10,11-dihydro dibenzo[b,f]oxepin-2-yl)-acetic acid in 5 ml of dry tetrahydrofuran were added 4 drops of oxalyl chloride, and the mixture was stirred with ice-cooling. To the mixture were added 1 drop of dimethylformamide 1.75 hours later, 4 drops of oxalyl chloride 4 hours later and 1% ammonia in 5 ml tetrahydrofuran 6 hours later, and the resulting mixture was stirred for 17 hours at room temperature. To this was added water, and the mixture was extracted with ethyl acetate. The extract was washed with a 1% sodium hydroxide solution and then with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was recrystallized from ethyl acetate to yield 48 mg (yield: 48%) of (10,11-dihydro dibenzo[b,f]oxepin-2-yl)-acetamide as colorless crystals having a melting point of 205°-206° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a 1% sodium hydroxide solution
  4. dry with materialwith a saturated sodium chloride solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain a residue, which
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-57db997687a4417c90b5ffc7c7b4cf52
Source dataset
uspto-grants-1981_04
Patent number
US04263437

Reaction notes

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