Hydrochloric Acid → 3-Formylbenzamide

HRID 841041노트

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HRID 841041 반응식
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])(O)=[O:8].[NH4+:18].[OH-].Cl>C(Cl)Cl.CN(C=O)C>[C:7]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])(=[O:8])[NH2:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 120773-CarboxybenzaldehydeHCID 14923Ammonium HydroxideHCID 65578Oxalyl chloride

생성물 1

HCID 106306703-Formylbenzamide수율 65.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

Oxalyl chloride (13.3 mL, 152 mmol) and DMF (50 μL) were added to suspension of 3-carboxybenzaldehyde (11.4 g, 76.2 mmol) in 200 mL CH2Cl2 and stirred at 23° C. for 18 h. The resulting clear solution was concentrated, dissolved in 100 mL CH2Cl2, and concentrated again. The crude acid chloride was dissolved in 20 mL THF, poured into a mixture of concentrated NH4OH (26 mL, 381 mmol) with 100 mL crushed ice, and allowed to warm to 23° C. with stirring. The mixture was acidified with conc. HCl to pH ˜3, then concentrated to remove THF. The resulting aqueous suspension was filtered and the white solid product dried under vacuum to give 7.4 g (65%) of 3-carbamoyl-benzaldehyde compound 1a: 1H NMR (DMSO-d6)δ 10.06 (1 H, s), 8.40 (1 H, s), 8.19 (1 H, s), 8.17 (1 H, d, J=6.6 Hz), 8.04 (1 H, d, J=7.7 Hz), 7.69 (1 H, t, J=7.7 Hz), 7.56 (1 H, s); IR (KBr pellet) 3391, 3205, 1711, 1694, 1664, 1385, 1217. Anal. (C8H7NO2•0.1H2O) C, H, N.

후처리

  1. concentrationThe resulting clear solution was concentrated
  2. dissolutiondissolved in 100 mL CH2Cl2
  3. concentrationconcentrated again
  4. dissolutionThe crude acid chloride was dissolved in 20 mL THF
  5. customcrushed ice
  6. temperatureto warm to 23° C.
  7. stirringwith stirring
  8. concentrationconcentrated
  9. customto remove THF
  10. filtrationThe resulting aqueous suspension was filtered
  11. customthe white solid product dried under vacuum

출처 및 근거

ORD 기록
ord-5446c184cbf049419f1329529c7ed678
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369226B1

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