Sodium Chloride → HCID 23691091, compound

HRID 1296167Notes

Reaction equation

HRID 1296167 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:13])[O:9][CH:10]([CH3:12])[CH3:11])=[CH:3][CH:2]=1.Cl[S:21]([OH:24])(=[O:23])=[O:22].C(=O)=O.CO.[Na+:30].[Cl-]>ClCCl>[Na+:30].[CH:10]([O:9][C:8]([NH:7][C:4]1[CH:5]=[CH:6][C:1]([C:14]2[CH:15]=[CH:16][C:17]([S:21]([O-:24])(=[O:23])=[O:22])=[CH:18][CH:19]=2)=[CH:2][CH:3]=1)=[O:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24638Chlorosulfonic acid2×HCID 15965628HCID 15965628, compoundHCID 21973728Carbon dioxide methanol

Product 1

HCID 23691091HCID 23691091, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A suspension of isopropyl biphenyl-4-ylcarbamate (256 g, 1 mol) in dichloromethane (2000 ml) was cooled to −10° C. and chlorosulfonic acid (350 g, 200 ml, 3 mol) was added dropwise with stirring within 25 min with gentle cooling using a dry ice-methanol bath. The internal temperature was kept below −4° C. Subsequently, the dry ice-methanol bath was replaced by an ice bath and the mixture was stirred at from 3° C. to 14° C. for 1.5 h. Afterward, chlorosulfonic acid (175 ml, 2.6 mol) was again added at from 2° C. to 3° C., the mixture was stirred again for 30 min and then worked up. To this end, a mixture of ice (5 kg), methylene chloride (1000 ml) and concentrated NaCl solution (1300 ml) was initially charged under vigorous stirring and the reaction mixture was added slowly. The precipitated solid was filtered off with suction and dried at 45° C. under reduced pressure. 329 g (92%) of 4′-isopropoxycarbonylaminobiphenyl-4-sulfonic acid sodium salt were obtained as a white, crystalline powder, m.p.>260° C.,

Workup

  1. temperaturewith gentle cooling
  2. customwas kept below −4° C
  3. stirringthe mixture was stirred at from 3° C. to 14° C. for 1.5 h
  4. stirringthe mixture was stirred again for 30 min
  5. additionwas initially charged
  6. stirringunder vigorous stirring
  7. additionthe reaction mixture was added slowly
  8. filtrationThe precipitated solid was filtered off with suction
  9. customdried at 45° C. under reduced pressure

Sources & evidence

ORD record
ord-c13534026af14e9b9e4b4fb6e52718e0
Source dataset
uspto-grants-2007_07
Patent number
US07244845B2

Reaction notes

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