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Dimethyl Sulfoxide → Aminocyclopyrachlor-methyl

HRID 218306
ノート
印刷プレビュー

反応式

HRID 218306 の反応式
[CH2:1](N(CCCC)CCCC)CCC.CS(C)=O.O.[NH2:19][C:20]1[N:25]=[C:24]([CH:26]2[CH2:28][CH2:27]2)[N:23]=[C:22]([C:29]([OH:31])=[O:30])[C:21]=1[Cl:32].BrC>O>[NH2:19][C:20]1[N:25]=[C:24]([CH:26]2[CH2:28][CH2:27]2)[N:23]=[C:22]([C:29]([O:31][CH3:1])=[O:30])[C:21]=1[Cl:32]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6323Methyl BromideHCID 7622TributylamineHCID 670843376-Amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monohydrate

生成物 1

HCID 16725794Aminocyclopyrachlor-methyl収率 81%

試薬・触媒・溶媒 1

HCID 962Water
溶媒

反応条件

温度
5 °C

実験手順

A 200-mL reactor equipped with a 10-mL jacketed addition funnel below a cold-finger condenser at −10° C., a nitrogen inlet and overhead stirring was charged with tributylamine (20.4 g, 0.11 mol) and DMSO (45 mL). The mixture was stirred at 25° C., and 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monohydrate (23.1 g, 0.1 mol) was added in portions. The reaction mixture was stirred at 30° C. while bromomethane (13.3 g, 8 mL, 0.14 mol) was condensed into the jacketed addition funnel and then added to the reaction mixture over 30 minutes. The mixture was stirred for an additional 3 h and then added over about 30 minutes to a reactor charged with water (200 mL) at 25° C. The resulting slurry was cooled to 5° C. and filtered. The filtered cake was washed with water (2×30 mL) and dried at 60° C. in a vacuum-oven for 16 h to give 18.4 g (81% yield) of the title compound as an off-white solid melting at 147-148° C.

後処理

  1. customA 200-mL reactor equipped with a 10-mL
  2. additionaddition funnel below a cold-finger condenser at −10° C.
  3. stirringThe mixture was stirred at 25° C.
  4. customcondensed into the jacketed addition funnel
  5. additionadded to the reaction mixture over 30 minutes
  6. stirringThe mixture was stirred for an additional 3 h
  7. additionadded over about 30 minutes to a reactor
  8. filtrationfiltered
  9. washThe filtered cake was washed with water (2×30 mL)
  10. customdried at 60° C. in a vacuum-oven for 16 h

出典と根拠

ORDレコード
ord-1100957dc1934ba6860c3c3022d300df
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198442B2

反応ノート

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