Phosphorus oxychloride → HCID 11122740, 화합물

HRID 353028노트

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HRID 353028 반응식
O=P(Cl)(Cl)Cl.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:31]([O:30][C:26]1[C:25]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:29]=[CH:28][C:27]=1[CH:14]=[O:15])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 205433631,1',1''-[Benzene-1,2,3-triyltris(oxymethylene)]tribenzene

생성물 1

HCID 11122740HCID 11122740, 화합물수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

Kolonits, P. et al., Acta Chim. Hung. 113:367 (1983). POCl3 (155 mL, 1.66 mol) was slowly added to N-methylformanilide (175 mL, 1.4 mol) at room temperature under Ar which resulted in formation of a yellow solid. After 2 h, the solid was treated with a solution of 1,2,3-tribenzyloxybenzene 8 (20 g, 51 mmol) in anhydrous DMF (40 mL) and heated to 60° C. After 3 h, the resulting crimson solution was cooled to room temperature and then poured into ice water (3 L) with vigorous stirring for 12 h. The resulting brown precipitate was filtered, washed with hexanes (3×100 mL) and finally recrystallized from MeOH to afford 10 (19.8 g, 93%) as a white powder. mp 73-74° C. 1H NMR (CDCl3): δ10.11 (s, 1 H), 7.57 (d, J=9 Hz, 1 H), 7.44-7.28 (m, 15 H), 6.83 (d, J=9 Hz, 1 H), 5.21(s, 2 H), 5.16 (s, 2 H), 5.08 (s, 2 H); 13C NMR (CDCl3): δ188.8, 158.5, 155.9, 141.1, 136.9, 136.2, 135.8, 128.6, 128.5 (2), 128.3 (2) 128.2, 127.5, 124.0, 109.1, 76.8, 75.5, 70.9. Anal. Calcd for C28H24O4: C, 79.22; H, 5.70. Found: C, 79.17; H, 5.80. HRMS (FAB) calcd for C28H24O4 (M+H+): 424.1675. Found: 424.1669.

후처리

  1. customresulted in formation of a yellow solid
  2. waitAfter 3 h
  3. temperaturethe resulting crimson solution was cooled to room temperature
  4. filtrationThe resulting brown precipitate was filtered
  5. washwashed with hexanes (3×100 mL)
  6. customfinally recrystallized from MeOH

출처 및 근거

ORD 기록
ord-5fc7101e11674ed1aa37d612b11771e0
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750049B1

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