Ammonia → Aminocyclopyrachlor-methyl

HRID 249659노트

반응식

HRID 249659 반응식
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[Cl:14].S(Cl)(Cl)=O.O.N.[CH3:21]O>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH3:21])=[O:12])[C:3]=1[Cl:14]

참가 물질

7

반응물 5

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 17747875Aminocyclopyrachlor2회

생성물 1

HCID 16725794Aminocyclopyrachlor-methyl

시약·촉매·용매 1

HCID 1118Sulfuric Acid촉매

반응 조건

온도
5 °C

실험 절차

To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step D1 or D2 of Example 2) (2.0 g, 8.5 mmol) in methanol (20 mL) was added dropwise thionyl chloride (4 mL, 70 mmol). The mixture was heated at reflux for 24 h. Concentrated sulfuric acid (5 drops) was added, and the reaction mixture was heated at reflux for 16 h. After the mixture was cooled, water (30 mL) was added, and aqueous ammonia (28%, 10 mL) was added dropwise. The mixture was cooled to 5° C., and the solid was isolated by filtration, washed with water and dried in a vacuum oven at 40° C. to afford the title product (2.3 g), a compound of the present invention.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 16 h
  5. temperatureAfter the mixture was cooled
  6. customthe solid was isolated by filtration
  7. washwashed with water
  8. customdried in a vacuum oven at 40° C.

출처 및 근거

ORD 기록
ord-55af0cb4747e42688cbc36ab4b90fef9
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863220B2

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