Hydrochloric Acid → HCID 15307970, compound

HRID 1288957Notes

Reaction equation

HRID 1288957 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[NH:8][CH2:7][C:6]=2[CH:16]=1.[CH3:17][C:18]1[CH:35]=[CH:34][CH:33]=[CH:32][C:19]=1[C:20]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)=[O:21].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]([C:27]([C:26]3[CH:25]=[CH:24][C:23]([NH:22][C:20](=[O:21])[C:19]4[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=4[CH3:17])=[CH:31][CH:30]=3)=[O:28])[CH2:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 15410465HCID 15410465, compound

Product 1

HCID 15307970HCID 15307970, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.229 g (1.0 mmol) of 2-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine in 1.0 ml of pyridine under nitrogen is added 0.30 g (1.1 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride. The mixture is stirred at room temperature for 1 hour, heated on a steam bath for 5 minutes and 8 ml of 2N HCl added. The mixture is extracted with ethyl acetate and the extract washed three times with 1 ml of 1N sodium bicarbonate. The organic layer is dried (MgSO4) and the solvent removed. The residue is crystallized from ethyl acetate-hexane to give 0.24 g of crystals, m.p. 207°-208° C. Anal. Calc'd for C28H2N2 O3Cl: C,71.9; H,4.5; N,6.0; Cl,7.6. Found: C,71.6; H,4.6; N,5.9; Cl,7.4.

Workup

  1. temperatureheated on a steam bath for 5 minutes
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe extract washed three times with 1 ml of 1N sodium bicarbonate
  4. dry with materialThe organic layer is dried (MgSO4)
  5. customthe solvent removed
  6. customThe residue is crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-27f42e4b499d4c3e9446b16c2a47a2e9
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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