Formamide → 2,6-Naphthalenedicarboxamide

HRID 388184

반응식

HRID 388184 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][C:7](C(OC)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17]C)=O.[CH:19]([NH2:21])=[O:20].C[N:23](C)C=O.C[O-].[Na+]>CO>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:19]([NH2:21])=[O:20])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([NH2:23])=[O:17]

참가 물질

6

반응물 4

HCID 713FormamideHCID 6228DimethylformamideHCID 61225Dimethyl-2,6-naphthalenedicarboxylateHCID 10942334Sodium Methoxide

생성물 1

HCID 4460272,6-Naphthalenedicarboxamide

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
100 °C

실험 절차

2,6-Naphthalenedicarboxamide (CAS #46711-49-3) was prepared as follows. To a two liter three neck round-bottom flask fitted with a mechanical stirrer, addition funnel and condenser/Dean Stark apparatus, with a nitrogen inlet was charged 85.4 grams (0.35 mol) dimethyl 2,6-naphthalenedicarboxylate, 105.3 grams (2.34 mol) formamide, and 200 mls of anhydrous N,N-dimethylformamide. The flask contents were heated to 100 degrees C. under a nitrogen atmosphere and held for one hour. One hundred ml of a 25 wt. % solution of sodium methoxide in methanol was added through the addition funnel in four approximately equal portions. The flask contents were then heated for four hours at 100 degrees C. during which time methanol was being condensed and removed. The flask was cooled to room temperature and one liter of isopropyl alcohol was added in two 500 ml increments. After the resulting mixture was stirred for 15 minutes it was allowed to settle for one hour. Crystallized solid material was collected by filtration and air dried in the filter for 2 hours. The recovered off-white colored product weighed 112.7 grams. The solid was washed three times in deionized water and twice in methanol which yielded 71.4 grams of greater than 98% pure product. Melting point: 347-349 degrees C.; 1H NMR: This compound is insoluble in all common NMR solvents and only sparingly soluble in DMSO-d6. (DMSO-d6) δ 8.53 ppm (broad s), 8.21 ppm (broad s), 8.07 ppm (complex multi. from 8.09−8.00 ppm), 7.55 ppm (broad s), also 3.38 ppm (water), and 2.51 (DMSO); MS m/z 214 [M].

후처리

  1. temperatureThe flask contents were then heated for four hours at 100 degrees C
  2. customcondensed
  3. customremoved
  4. temperatureThe flask was cooled to room temperature
  5. additionone liter of isopropyl alcohol was added in two 500 ml increments
  6. waitto settle for one hour
  7. customCrystallized solid material
  8. filtrationwas collected by filtration and air
  9. customdried in the
  10. filtrationfilter for 2 hours
  11. washThe solid was washed three times in deionized water

출처 및 근거

ORD 기록
ord-e100181f9f224e50ba86becbcccf6469
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377530B2

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