Hydrochloric Acid → phenyl N-(2-biphenylylsulfonyl)carbamate

HRID 745857Notes

Reaction equation

HRID 745857 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH2:18])(=[O:17])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19](=O)([O:27]C1C=CC=CC=1)[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CN(C)C=O>[C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19](=[O:27])[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7597Diphenyl carbonateHCID 24758Sodium hydrideHCID 123715202-Phenylbenzene-1-sulfonamide

Product 1

HCID 13590973phenyl N-(2-biphenylylsulfonyl)carbamateYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (2.6 g) was added to dry dimethylformamide (200 ml), and at less than 10° C., a solution of 2-phenylbenzenesulfonamide (23.3 g) in dimethylformamide (50 ml) was added. The mixture was then stirred at room temperature for 1 hour, and diphenyl carbonate (21.4 g) was added at room temperature. The mixture was further stirred at room temperature for 1 hour. Then, after the whole mixture was added to ice water, the mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was dehydrated, and ethyl acetate was distilled off under reduced pressure to give phenyl N-(2-biphenylylsulfonyl)carbamate (35 g) as a solidified desired compound represented by the following formula. mp. 114°-117° C. ##STR11##

Workup

  1. stirringThe mixture was further stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. distillationethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b451aa9c8b1c4b67abab6a6e4f66cdaa
Source dataset
uspto-grants-1986_07
Patent number
US04600792

Reaction notes

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