Furfural → 3-Furfurylideneamino-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606616Notes

Reaction equation

HRID 1606616 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:15])[C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1>O>[CH:16](=[N:15][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7362FurfuralHCID 189525243-Methylsulfonyl-4-chloro-5-aminobenzoic acid

Product 1

HCID 538687383-Furfurylideneamino-4-chloro-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methylsulfonyl-4-chloro-5-aminobenzoic acid (3.0 g.; 0.012 mole) and furfural (50 ml.) is heated to 70°-80° C. on a water bath. The water formed during the reaction is azeotropically distilled with the excess furfural at 15 mm Hg. pressure during a one hour period. The reaction mixture is cooled and triturated with carbon tetrachloride (100 ml.) to yield 3.6 g. (90%) of 3-furfurylideneamino-4-chloro-5-methylsulfonylbenzoic acid which melts at 221° C. and is used in Step E without further purification.

Workup

  1. temperatureis heated to 70°-80° C. on a water bath
  2. distillationis azeotropically distilled with the excess furfural at 15 mm Hg
  3. temperatureThe reaction mixture is cooled
  4. customtriturated with carbon tetrachloride (100 ml.)
  5. customto yield 3.6 g
  6. custom(90%) of 3-furfurylideneamino-4-chloro-5-methylsulfonylbenzoic acid which melts at 221° C. and is used in Step E without further purification

Sources & evidence

ORD record
ord-6eafde4d116a4ee6b2d5aadda9d05c95
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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