Urea → HCID 19995894, 화합물

HRID 235621

반응식

HRID 235621 반응식
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=[O:15].[Na+].NC(N)=O.[OH-].[Na+]>S(=O)(=O)(O)O.O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu-]=O>[S:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:15])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

참가 물질

9

반응물 4

HCID 1176UreaHCID 14798Sodium HydroxideHCID 107742064-ThiomorpholinoanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 19995894HCID 19995894, 화합물

시약·촉매·용매 4

HCID 9837674Copper(II) nitrate trihydrate촉매HCID 178419072HCID 178419072, 화합물촉매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

2.34 g of 4-(p-aminophenyl)-tetrahydro-4H-1,4-thiazine are dissolved in 12 ml of 35 percent sulfuric acid, 12 g of ice are added thereto, a cold solution of 1.05 g of sodium nitrite in 12 ml of water is then slowly introduced under the surface and the mixture is stirred for 5 minutes at about 0°. Thereafter, there are added 60 mg of urea, a solution of 144 g of copper(II) nitrate trihydrate in 420 ml of water and finally while stirring vigorously 1.59 g of copper(I) oxide. The mixture is stirred for 5 minutes, adjusted to about pH 6 with sodium hydroxide solution and extracted three times with 600 ml of dichloromethane each time and once with 600 ml of dichloromethane/ethanol (4:1). The organic phases are washed twice with 300 ml of water each time, dried over sodium sulfate and evaporated. The crude product is chromatographed on 400 g of silica gel with dichloromethane which contains 5% acetone. The material obtained is recrystallized from dichloromethane/methanol/ether, whereby there is obtained p-(tetrahydro-4H-1,4-thiazin-4-yl)phenol of melting point 155°-157°.

후처리

  1. stirringThe mixture is stirred for 5 minutes
  2. extractionextracted three times with 600 ml of dichloromethane each time
  3. washThe organic phases are washed twice with 300 ml of water each time
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude product is chromatographed on 400 g of silica gel with dichloromethane which
  7. customThe material obtained
  8. customis recrystallized from dichloromethane/methanol/ether

출처 및 근거

ORD 기록
ord-ce63a61e09a6402c82d225931aaf26ae
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640918

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