Hydrochloric Acid → Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

HRID 14000

반응식

HRID 14000 반응식
N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[ClH:21].N([O-])=O.[Na+].[S:26](=[O:28])=[O:27]>C(O)(=O)C.O>[Cl:21][S:26]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:28])=[O:27]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]BenzoateHCID 23668193Sodium Nitrite

생성물 1

HCID 22593631Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate (XXXI, PREPARATION 10, 1.11 g, 4 mmol) is added to a mixture of water (5 mL) and concentrated hydrochloric acid (1 mL). Sodium nitrite (0.276 g, 4 mmol) is added to the mixture slowly at 0 degrees C. The mixture is then added to an acetic acid solution (5 mL) of CuCl2.2H2O saturated with sulfur dioxide. The mixture is stirred for 0.5 hours and poured into ice water. The mixture is extracted with ethyl acetate. The organic phase is separated and washed with saturated sodium bicarbonate, water, and saline and dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 8.69, 8.38, 8.20, 4.01, 3.49, 3.14, 1.72, 159, 1.01 and 0.79; MS (ESI+) for C15H20ClNO5S m/z (M+H)+=362.2

후처리

  1. extractionThe mixture is extracted with ethyl acetate
  2. customThe organic phase is separated
  3. washwashed with saturated sodium bicarbonate, water, and saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8acc97aef642495381b2df7e9ffa2515
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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