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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 2057889
ノート
印刷プレビュー

反応式

HRID 2057889 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 122586463-AminochromoneHCID 128903222-methyl-4-(1-pyrrolidinyl)-2H-1,2-benzothiazine 1,1-dioxide

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140
Toluene
溶媒
HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b886ba364b9b424c9ac4de2e3767cc47
出典データセット
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04213980

反応ノート

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