Carbon Disulfide → 5-Isothiocyanato-3-methoxymethylisoquinoline

HRID 443814ノート

反応式

HRID 443814 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][O:13][CH3:14])[N:6]=[CH:7]2.C(N(CC)CC)C.[C:22](=S)=[S:23].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[N:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][O:13][CH3:14])[N:6]=[CH:7]2)=[C:22]=[S:23]

参加物

6

反応物 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 128748525-Amino-3-methoxymethylisoquinoline

生成物 1

HCID 128748545-Isothiocyanato-3-methoxymethylisoquinoline

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒3 回

実験手順

A solution of 5-amino-3-methoxymethylisoquinoline (22.9 g) in pyridine (80 cc) is added dropwise, whilst stirring and at a temperature of about -10° C., to a solution of triethylamine (17 cc) and carbon disulphide (55 cc) in pyridine (80 cc). After 4 hours at -10° C., a solution of dicyclohexylcarbodiimide (25.2 g) in pyridine (80 cc) is added dropwise. Stirring is maintained for 3 hours at a temperature which changes from -10° to 20° C., and then for 20 hours at a temperature of about 20° C. The mixture is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg), the residue is taken up in methylene chloride (800 cc), and insoluble material is removed by filtration and the filtrate is evaporated to dryness at 40° C. under reduced pressure (40 mm Hg). The residue is taken up in diisopropyl ether (1 liter; an insoluble material is removed by filtration and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). 5-Isothiocyanato-3-methoxymethylisoquinoline (18.5 g), m.p. 88° C., is obtained.

後処理

  1. temperatureis maintained for 3 hours at a temperature which
  2. customchanges from -10° to 20° C.
  3. waitfor 20 hours at a temperature of about 20° C
  4. customThe mixture is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg)
  5. custominsoluble material is removed by filtration
  6. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (40 mm Hg)
  7. customan insoluble material is removed by filtration
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)

出典と根拠

ORDレコード
ord-9cbb245508844cb2b76b11161402d370
出典データセット
uspto-grants-1981_04
特許番号
US04261992

反応ノート

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