Benzenesulfonyl chloride → HCID 178481967, compound

HRID 2082782Notes

Reaction equation

HRID 2082782 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-:11].[NH2:12][C:13]1[N:17]2[C:18]3[C:37](Br)=[CH:36][C:35](CC)=[CH:34][C:19]=3[C:20]([C:24]3[CH:29]=[CH:28][C:27](C(F)(F)F)=[CH:26][CH:25]=3)=[N:21][CH:22](C)[CH:16]2[N:15]([CH2:41]CC)[NH+:14]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[OH-:8].[C:1]1([S:7]([NH:12][C:13]2[N:17]3[C:18]4[CH:37]=[CH:36][C:35]([Cl:11])=[CH:34][C:19]=4[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:21][CH2:22][CH:16]3[N:15]([CH3:41])[NH+:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178456697HCID 178456697, compound

Product 1

HCID 178481967HCID 178481967, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice cold stirred solution of 0.388 g. (0.0022 mole) of benzenesulfonyl chloride in 15 ml. of dried pyridine, 0.721 g. (0.002 mole) of 1-amino-8-chloro-3-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepinium chloride (VI) is added. The resulting mixture is kept in an ice bath for about 15 hours and then allowed to warm to room temperature and stand for about 6 hours. It is then poured into cold, dilute aqueous sodium bicarbonate solution and extracted with chloroform. The extract is washed with brine, dried with sodium sulfate and concentrated. The residue is crystallized to give 1-benzenesulfonamido-8-chloro-3-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepinium hydroxide inner salt (X).

Workup

  1. waitstand for about 6 hours
  2. extractionextracted with chloroform
  3. washThe extract is washed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized

Sources & evidence

ORD record
ord-6c04381fc73e43858d0f7f8c6d33b23d
Source dataset
uspto-grants-1978_04
Patent number
US04082761

Reaction notes

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