Hydrochloric Acid → 4-Isothiocyanato-2-chlorobenzoic acid

HRID 511906노트

반응식

HRID 511906 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 227310064-Isothiocyanato-2-chlorobenzoic acid수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e5a2268ac35049b8a131cbc603ce8400
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102602B2

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