Hydrochloric Acid → HCID 178506334, compound

HRID 2199501Notes

Reaction equation

HRID 2199501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[Cl:16].[F:19][C:20]([F:31])([F:30])[C:21]([F:29])([F:28])[C:22]([F:27])([F:26])[C:23](O)=O.Cl>>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[CH:6][C:5]2[NH:17][C:23]([C:22]([F:26])([F:27])[C:21]([F:28])([F:29])[C:20]([F:31])([F:30])[F:19])=[N:18][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9777Heptafluorobutyric acidHCID 99722634-Chloro-5-(2,3-dichlorophenoxy)benzene-1,2-diamine

Product 1

HCID 178506334HCID 178506334, compound

Conditions

Temperature
110 °C

Procedure

Compound number 140 (i.e., 6-chloro-5-(2,3-dichlorophenoxy)-2-heptafluoropropylbenzimidazole) was prepared as follows. 4-chloro-5-(2,3-dichlorophenoxyl)benzene-1,2-diamine (150 mg, 0.49 mmol, 1.00 equiv), heptafluorobutanoic acid (15 mL) and hydrogen chloride (3 mL) was placed into a 100-mL round-bottom flask. The resulting solution was stirred overnight at 110° C. in an oil bath. The reaction mixture was cooled to room temperature. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). The crude product was re-crystallized from EA/hexane in the ratio of 1/1. This resulted in 63.4 mg (27%) of 6-chloro-5-(2,3-dichlorophenoxy)-2-heptafluoropropylbenzimidazole as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
  3. washThe resulting mixture was washed with 3×100 mL of brine
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe crude product was re-crystallized from EA/hexane in the ratio of 1/1
  6. customThis resulted in 63.4 mg (27%) of 6-chloro-5-(2,3-dichlorophenoxy)-2-heptafluoropropylbenzimidazole as a white solid

Sources & evidence

ORD record
ord-bd14173676fa485d833e685fb3bfe541
Source dataset
uspto-grants-2016_06
Patent number
US09359305B2

Reaction notes

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