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

HRID 76295

반응식

HRID 76295 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>CC#N.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 128C) in MeCN (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 overnight and then extracted with dichloromethane (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 dichloromethane (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-fe6bedb05c764f489000b06c81fddb89
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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