Sodium hydride → 5-Bromo-6-fluorobenzo[d]thiazol-2-amine

HRID 2068676ノート

反応式

HRID 2068676 の反応式
[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5](F)=[C:6]([NH:8][C:9]([NH2:11])=[S:10])[CH:7]=1.[H-].[Na+]>CN1C(=O)CCC1>[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:10][C:9]([NH2:11])=[N:8][C:6]=2[CH:7]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 59603071(5-Bromo-2,4-difluoro-phenyl)-thiourea

生成物 1

HCID 596030945-Bromo-6-fluorobenzo[d]thiazol-2-amine収率 52%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

To a solution of (5-Bromo-2,4-difluoro-phenyl)-thiourea (0.75 g, 2.80 mmol) in NMP (5.0 mL) was added NaH (0.17 g, 4.21 mmol, 60% dispersion in oil) portion wise. The reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then poured onto crushed ice and extracted with EtOAc (3×50 mL). The combined organics was evaporated to get the crude residue that was purified over silica gel (100-200 M, 12% EtOAc-Hexane) to obtain the desired compound (0.36 g, 52%). 1H-NMR (400 MHz, DMSO-d6): δ 7.57 (d, J=6.40 Hz, 1H), 7.66 (br s, 2H) and 7.79 (d, 8.80 Hz, 1H).

後処理

  1. additionThe reaction mixture was then poured
  2. customonto crushed ice
  3. extractionextracted with EtOAc (3×50 mL)
  4. customThe combined organics was evaporated
  5. customto get the crude residue that
  6. customwas purified over silica gel (100-200 M, 12% EtOAc-Hexane)

出典と根拠

ORDレコード
ord-6098fcab77a7446b9265eec6b53918d6
出典データセット
uspto-grants-2012_10
特許番号
US08299065B2

反応ノート

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