Hydrochloric Acid → 2-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606608Notes

Reaction equation

HRID 1606608 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[NH2:17][CH2:18][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+].Cl>O.C(COC)OC.C(N(CC)CC)C>[C:24]([C:22]1[O:23][C:19]([CH2:18][NH:17][C:2]2[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=1)([OH:26])=[O:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2210136551521-75-6HCID 568075445-(Aminomethyl)furan-2-carboxylic acid hydrochloride

Product 1

HCID 215439632-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2,4-dichloro-5-methylsulfonylbenzoic acid (3.50 g.; 0.013 mole), 5-aminomethyl-2-furancarboxylic acid hydrochloride (4.83 g.; 0.027 mole), triethylamine (11.5 ml.), and glyme (25 ml.) is heated to 140°-150° C. for 24 hours. Solid sodium bicarbonate (5.0 g.) is added and refluxing is continued for another 24 hours. The mixture is poured into water (150 ml.) and acidified by the addition of 6N hydrochloric acid. The tan solid is collected, washed with water, and dried, 1.20 g., m.p. 269°-272° C. Recrystallization from acetonitrile gives 2-(5-carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid, m.p. 263.5°-265.5° C. (dec.).

Workup

  1. temperatureis heated to 140°-150° C. for 24 hours
  2. temperaturerefluxing
  3. customThe tan solid is collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-373033f9ef074426958868561f9e26ad
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

Loading…