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Phosgene → 2-methyl-N-(4-oxo-4H-1-benzopyran-3-yl)-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 2286202
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HRID 2286202 반응식
[C:1](Cl)(Cl)=[O:2].[CH3:5][N:6]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=2[S:7]1(=[O:22])=[O:21].C(N(CC)CC)C.[NH2:30][C:31]1[C:36](=[O:37])[C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[O:33][CH:32]=1>C1(C)C=CC=CC=1.O1CCCC1>[CH3:5][N:6]1[C:11]([C:1]([NH:30][C:31]2[C:36](=[O:37])[C:35]3[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=3[O:33][CH:32]=2)=[O:2])=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=2[S:7]1(=[O:22])=[O:21]
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HCID 6371PhosgeneHCID 8471TriethylamineHCID 122586463-AminochromoneHCID 128903222-methyl-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine 1,1-dioxide

생성물 1

HCID 205422222-methyl-N-(4-oxo-4H-1-benzopyran-3-yl)-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8028Tetrahydrofuran용매3회

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온도
-40 °C

실험 절차

The starting material can be prepared for example as follows: A solution of 2.5 g (0.025 mole) of phosgene in toluene is diluted with 50 ml of dry tetrahydrofurane and then cooled to a temperature of -40° C. A solution of 6.6 g (0.025 mole) of 2-methyl-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine 1,1-dioxide and 2.5 g (0.025 mole) of triethylamine in 200 ml of tetrahydrofurane is then added slowly, with stirring, at a temperature of -40° to +55° C. in the course of 30 minutes. The reaction mixture is stirred for 12 hours at room temperature, then cooled to 10° C., and subsequently a suspension of 6.25 g (0.05 mole) of 3-amino-4-oxo-4H-1-benzopyrane in 100 ml of tetrahydrofurane is added slowly. The temperature of the reaction mixture is allowed to rise to room temperature. The reaction mixture is then stirred for 72 hours and poured into ice-water. The precipitate is collected by suction and crystallised from tetrahydrofurane, affording pure crystalline 2-methyl-N-(4-oxo-4H-1-benzopyran-3-yl)-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide. 2-Methyl-3,4-dihydro-4-oxo-N-(6-chloro-7-methyl-4-oxo-4H-1-benzopyran-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide can be obtained in analogeous manner starting from 2-methyl-N-(6-chloro-7-methyl-4-oxo.4H-1-benzopyran- 3-yl)-4-(1-pyrrolidinyl)-1,2-benzothiazine-3-carboxamide 1,1-dioxide.

후처리

  1. stirringThe reaction mixture is stirred for 12 hours at room temperature
  2. temperaturecooled to 10° C.
  3. additionis added slowly
  4. customto rise to room temperature
  5. stirringThe reaction mixture is then stirred for 72 hours
  6. customThe precipitate is collected by suction
  7. customcrystallised from tetrahydrofurane

출처 및 근거

ORD 기록
ord-11246e6abfef48eb9938ee385008d101
출처 데이터셋
uspto-grants-1982_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04327091

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