Hydrochloric Acid → HCID 11324315, compound

HRID 1464557Notes

Reaction equation

HRID 1464557 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])O.[Na+].[CH2:17]([O:25][C:26](Cl)=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].Cl>O.CO>[CH2:17]([O:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7])=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 46494-Aminosalicylic AcidHCID 81956Carbonochloridic acid, octyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 11324315HCID 11324315, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 700 ml of methanol suspended 153 g of 4-aminosalicylic acid and 84 g of sodium hydrogen carbonate, 193 g of n-octylchloroformate was dropwise added over 2 hours at room temperature. After finishing dropwise addition, the mixture was further stirred for 2 hours at room temperature. An aqueous solution containing 30 g of concentrated hydrochloric acid and 1200 ml of water was added to the reaction mixture. Precipitated crystals were filtered and dried to obtain 300 g of desired 4-(n-octyloxycarbonylamino)salicylic acid as colorless crystals. Yield was 97%.

Workup

  1. additionwas dropwise added over 2 hours at room temperature
  2. additionaddition
  3. additionwas added to the reaction mixture
  4. customPrecipitated crystals
  5. filtrationwere filtered
  6. customdried

Sources & evidence

ORD record
ord-dabd672b1de843e4a7ec29622a0506f4
Source dataset
uspto-grants-1994_04
Patent number
US05306688

Reaction notes

Loading…