Water → HCID 13134776, compound

HRID 355104Notes

Reaction equation

HRID 355104 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[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([OH:19])=O.C(Cl)(=O)C(Cl)=O.C[N:27](C)C=O.O>O1CCCC1>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([NH2:27])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 12443712HCID 12443712, compound

Product 1

HCID 13134776HCID 13134776, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 mg of (10,11-dihydro dibenzo[b,f]thiepin-2-yl)-acetic acid in 5 ml of dry tetrahydrofuran were added 0.2 g of oxalyl chloride and a drop of dimethylformamide, and the mixture was stirred with ice cooling under a dry atmosphere for 3 hours. To the mixture was added 5 ml of tetrahydrofuran containing 1% ammonia, and the mixture was stirred under a dry atmosphere at room temperature for 14 hours. After the addition of water, 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, thereby obtaining 66 mg (yield: 66%) of (10,11-dihydro dibenzo[b,f]thiepin-2-yl)-acetamide as colorless crystals having a melting point of 188°-189° C.

Workup

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

Sources & evidence

ORD record
ord-f66f29cb64584c78a0ef0125dbbe9cd6
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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