2-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1) → 7-Methyl-9-oxothioxanthene-3-carboxylic acid

HRID 884329

반응식

HRID 884329 반응식
C(N)(=O)C(C)=C.O=S1C2C(=CC=CC=2)CC2C=CC=CC1=2.Cl.NCCCNC(=O)C(C)=C.[CH3:33][C:34]1[CH:47]=[C:46]2[C:37]([S:38][C:39]3[CH:40]=[C:41]([C:49]([OH:51])=[O:50])[CH:42]=[CH:43][C:44]=3[C:45]2=[O:48])=[CH:36][CH:35]=1.[Cl-].Cl.NCCCNC(=O)C(C)=C.C(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:33][C:34]1[CH:47]=[C:46]2[C:37]([S:38][C:39]3[CH:40]=[C:41]([C:49]([OH:51])=[O:50])[CH:42]=[CH:43][C:44]=3[C:45]2=[O:48])=[CH:36][CH:35]=1

참가 물질

6

반응물 4

HCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)HCID 86587294HCID 86587294, 화합물HCID 131729876HCID 131729876, 화합물HCID 131729877HCID 131729877, 화합물

생성물 1

HCID 108259057-Methyl-9-oxothioxanthene-3-carboxylic acid

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A methacrylamide-oxothioxanthene monomer (N-[3-(7-Methyl-9-oxothioxanthene-3-carboxamido)propyl]methacrylamide (MTA-APMA)) was first prepared. N-(3-aminopropyl)methacrylamide hydrochloride (APMA), 4.53 g (25.4 mmol), prepared as described in U.S. Pat. No. 5,858,653, Example 2, was suspended in 100 mL of anhydrous chloroform in a 250 mL round bottom flask equipped with a drying tube. 7-methyl-9-oxothioxanthene-3-carboxylic acid (MTA) was prepared as described in U.S. Pat. No. 4,506,083, Example D. MTA-chloride (MTA-Cl) was made as described in U.S. Pat. No. 6,007,833, Example 1. After cooling the slurry in an ice bath, MTA-Cl (7.69 g; 26.6 mmol) was added as a solid with stirring to the APMA-chloroform suspension. A solution of 7.42 mL (53.2 mmol) of TEA in 20 mL of chloroform was then added over a 1.5 hour time period, followed by a slow warming to room temperature. The mixture was allowed to stir 16 hours at room temperature under a drying tube. After this time, the reaction was washed with 0.1 N HCl and the solvent was removed under vacuum after adding a small amount of phenothiazine as an inhibitor. The resulting product was recrystallized from tetrahydrofuran (THF)/toluene (3/1) and gave 8.87 g (88.7% yield) of product after air drying. The structure of MTA-APMA was confirmed by NMR analysis.

후처리

  1. customequipped with a drying tube
  2. temperatureAfter cooling the slurry in an ice bath
  3. additionMTA-Cl (7.69 g; 26.6 mmol) was added as a solid
  4. washAfter this time, the reaction was washed with 0.1 N HCl
  5. customthe solvent was removed under vacuum
  6. additionafter adding a small amount of phenothiazine as an inhibitor
  7. customThe resulting product was recrystallized from tetrahydrofuran (THF)/toluene (3/1)

출처 및 근거

ORD 기록
ord-db09e34e3b024c8bbd1a417fe1e7cfaa
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08241656B2

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