Hydrochloric Acid → Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

HRID 1005270

반응식

HRID 1005270 반응식
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[N:16]([O-])=[O:17].[Na+].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][N:2]([C:9]1[CH:10]=[CH:11][C:12]([N:16]=[O:17])=[CH:13][CH:14]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 265936(Methyl-phenyl-amino)-acetic acid ethyl esterHCID 23668193Sodium Nitrite

생성물 1

HCID 12038854Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A solution of 15.5 g (80 mmol) of ethyl N-methyl-N-phenylglycinate in 80 g of ice and 40 mL of conc.HCl was stirred at 0-5° while a solution of 6 g (87 mmol) of NaNO2 in 40 mL of water was added dropwise over 30 min. After stirring at this temp. for 1 hr, a solution of 27 g (250 mmol) of Na2CO3 in 150 mL of water was added dropwise with cooling. The green solid was collected, washed with cold water, extracted into CH2Cl2, passed thorugh silica with CH2Cl2 to remove an impurity, and the product eluded with 10% ethyl acetate/CH2Cl2 to give 14.7 g (66 mmol, 83%) mp 55-56° after washing with 10% ethyl acetate/hexane. Anal. C11H14N2O3 (222): Calcd.: C,59.45; H,6,35; N,12.60. Found: C,59.46; H,6.14; N,12.49. MS(FD) m/z 222. 1H NMR(CDCl3)δ: 7.8,broad s,2H,ArH; 6.69,d,2H,ArH; 4.22,q,2H,CH2 --O; 4.20,s,2H,CH2 --N; 3.23,s,3H,CH3 --N; 1.27,t,3H,CH3 --C.

후처리

  1. additionwas added dropwise over 30 min
  2. temperaturewith cooling
  3. customThe green solid was collected
  4. washwashed with cold water
  5. extractionextracted into CH2Cl2
  6. customto remove an impurity
  7. customto give 14.7 g (66 mmol, 83%) mp 55-56°
  8. washafter washing with 10% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-bd1b2f43f2a6466e9d2d95111e299170
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054260

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