Cyanamide → Ethyl 5-chloro-N-cyano-2-methoxybenzimidate

HRID 254679

반응식

HRID 254679 반응식
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH:13]=1)[C:8](=[NH:12])[O:9][CH2:10][CH3:11].O.OP([O-])(O)=O.[Na+].O.O.O.O.O.O.O.OP([O-])([O-])=O.[Na+].[Na+].[N:37]#[C:38]N>C(#N)C.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH:13]=1)[C:8](=[N:12][C:38]#[N:37])[O:9][CH2:10][CH3:11]

참가 물질

7

반응물 4

HCID 9864CyanamideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 6096963Phosphoric acid, disodium salt, heptahydrateHCID 66851771Ethyl 5-chloro-2-methoxybenzimidate hydrochloride

생성물 1

HCID 86623446Ethyl 5-chloro-N-cyano-2-methoxybenzimidate수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of ethyl 5-chloro-2-methoxybenzimidate (1.3 g, 6.2 mmol, obtained after aqueous bicarbonate wash of Example 93D) in acetonitrile (2 mL) was added to a solution of sodium phosphate monobasic monohydrate (3.4 g, 24.7 mmol), sodium phosphate dibasic heptahydrate (3.3 g, 12.4 mmol) and cyanamide (0.52 g, 12.4 mmol) in water (20 mL). The reaction mixture was stirred at room temperature for overnight and then extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue contained about 30% of starting material. The residue was reprocessed with half the amounts of the reagents to drive the reaction to completion and that yielded 1.32 g (90%) of the title compound. MS (ESI+) m/z 239 (M+H)+.

후처리

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe reaction to completion

출처 및 근거

ORD 기록
ord-c99ce14ac92a491ca18385dac92c506d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875640B2

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