Phosphorus trichloride → 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

HRID 660045ノート

反応式

HRID 660045 の反応式
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.P(Cl)(Cl)Cl.C(Cl)Cl.CO>ClC1C=CC=CC=1>[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:6]

参加物

6

反応物 4

HCID 24387Phosphorus trichlorideHCID 34005(2-Thienylmethyl)amineHCID 21226129Dichloromethane methanolHCID 178524460HCID 178524460、化合物

生成物 1

HCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide収率 24.1%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
145 °C

実験手順

A suspension of 8.0 g (51.5 mmol) of 2-mercaptonicotinic acid, 5.8 g (51.5 mmol) of 2-(aminomethyl)-thiophene and 3.5 g (25.8 mmol) of phosphorus trichloride in chlorobenzene (260 ml) was heated for 3 h under reflux (145° C.). When the reaction solution had cooled to 60° C., filtration with suction was carried out at that temperature. The solid obtained was taken up in a DCM/MeOH mixture (3:1, vv, 300 ml) and washed with water (2×50 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. Crystallization of the residue from ethyl acetate yielded 3.1 g (12.4 mmol, 24%) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide.

後処理

  1. temperaturewas heated for 3 h
  2. temperatureWhen the reaction solution had cooled to 60° C.
  3. filtrationfiltration with suction
  4. customThe solid obtained
  5. washvv, 300 ml) and washed with water (2×50 ml)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization of the residue from ethyl acetate

出典と根拠

ORDレコード
ord-71eaedfebdef49b3b6b14a7596714464
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

反応ノート

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