Ammonia → Aminocyclopyrachlor-methyl

HRID 249659ノート

反応式

HRID 249659 の反応式
[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]

参加物

7

反応物 5

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 17747875Aminocyclopyrachlor2 回

生成物 1

HCID 16725794Aminocyclopyrachlor-methyl

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-55af0cb4747e42688cbc36ab4b90fef9
出典データセット
uspto-grants-2011_01
特許番号
US07863220B2

反応ノート

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