Hydrochloric Acid → 4-Isothiocyanato-2-chlorobenzoic acid

HRID 511906Notes

Reaction equation

HRID 511906 reaction equation
C(N(CC)CC)C.[C:8]([N:15]1[CH:19]=[CH:18]N=C1)(N1C=CN=C1)=[S:9].NC1C=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[C:23]([Cl:30])[CH:22]=1.Cl>O.C(Cl)Cl>[N:15]([C:19]1[CH:18]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[C:23]([Cl:30])[CH:22]=1)=[C:8]=[S:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 171544-Amino-2-chlorobenzoic acidHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 227310064-Isothiocyanato-2-chlorobenzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A methylene chloride solution (235 mL) of triethylamine (30.6 mL, 219.5 mmol) and thiocarbonyldiimidazole (23.01 g, 129.14 mmol) was dropped to a methylene chloride solution (130 mL) of 4-amino-2-chlorobenzoic acid (18.84 g, 109.82 mmol) under cooling with ice, followed by stirring for one hour while an internal temperature of at most 10° C. was maintained. 4M hydrochloric acid (120 mL, 480 mmol) was dropped so that the internal temperature became at most 10° C., followed by stirring under cooling with ice for one hour. Water (10 mL) was added, and the formed pink solid was collected by filtration, washed with water (100 mL) five times and dried under reduced pressure to obtain 4-isothiocyanato-2-chlorobenzoic acid as a colorless solid (21.36 g, yield: 91%, HPLC purity: 98.2%).

Workup

  1. temperatureunder cooling with ice
  2. temperaturewas maintained
  3. custombecame at most 10° C.
  4. stirringby stirring
  5. temperatureunder cooling with ice for one hour
  6. filtrationthe formed pink solid was collected by filtration
  7. washwashed with water (100 mL) five times
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e5a2268ac35049b8a131cbc603ce8400
Source dataset
uspto-grants-2015_08
Patent number
US09102602B2

Reaction notes

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