Hydrochloric Acid → HCID 67624348, compound

HRID 362335Notes

Reaction equation

HRID 362335 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12][CH2:11][C:10]=2[CH:20]=1)(=[O:5])=[O:4].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23].Cl>N1C=CC=CC=1>[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[N:12]([C:29](=[O:30])[C:28]3[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:33][CH:32]=3)[CH2:11][C:10]=2[CH:20]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 70060990HCID 70060990, compound

Product 1

HCID 67624348HCID 67624348, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.9 g of 10,11-dihydro-N,N-dimethyldibenz[b,f][1,4]oxazepine-2-sulfonamide and 0.55 g of 4-nitrobenzoyl chloride in 3 ml of pyridine is stirred for 7 hours. To the mixture is added 20 ml of 2N hydrochloric acid and the mixture is extracted with ethyl acetate. The extract is washed with 5 ml of 2N HCl and three times with 5 ml of 2N Na2CO3. The extract is dried (MgSO4) and filtered through a thin pad of hydrous magnesium silicate. The pad is washed with ethyl acetate and the filtrate concentrated to give 1.1 g of a yellow solid. Crystallization from dichloromethane-diisopropylether gives 0.62 g of crystals, m.p. 177°-178° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with 5 ml of 2N HCl and three times with 5 ml of 2N Na2CO3
  3. dry with materialThe extract is dried (MgSO4)
  4. filtrationfiltered through a thin pad of hydrous magnesium silicate
  5. washThe pad is washed with ethyl acetate
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3157f623a71749d0a7961ae84fc20167
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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