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Pyridine → N-(5-bromothiazol-2-ylcarbamoyl)-5-methylbenzo[b]thiophene-2-sulfonamide

HRID 1009001
ノート
印刷プレビュー

反応式

HRID 1009001 の反応式
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9](Cl)(=[O:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1.[O-:15][C:16]#[N:17].[Na+].N1C=CC=CC=1.Br.[NH2:26][C:27]1[S:28][C:29]([Br:32])=[CH:30][N:31]=1>C(#N)C>[Br:32][C:29]1[S:28][C:27]([NH:26][C:16]([NH:17][S:9]([C:7]2[S:6][C:5]3[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=3[CH:8]=2)(=[O:11])=[O:10])=[O:15])=[N:31][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 27947715-Methyl-1-benzothiophene-2-sulfonyl chloride

生成物 1

HCID 42634696N-(5-bromothiazol-2-ylcarbamoyl)-5-methylbenzo[b]thiophene-2-sulfonamide収率 78.2%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a suspension of 5-methyl-benzo[b]thiophenesulfonyl chloride (Maybridge, CAS: 90273-30-6, 0.37 g) in acetonitrile (5.0 mL) were added sodium cyanate (0.163 g) in one portion and pyridine (0.60 mL). The reaction mixture was stirred at rt for 3 h, then 2-amino-5-bromothiazole hydrobromide (0.286 g) was added in one portion. The mixture was stirred at rt for 4 h and quenched with 70% acetic acid (2.4 mL) and water (4.0 mL). The suspension was filtered, washed with waterlethanol and water, dried over P2O5 under high vacuum to obtain the desired compound (0.372 g) as a creamy solid. MS (ISN): m/e 430.1, 432.0 (M−H)−

後処理

  1. stirringThe mixture was stirred at rt for 4 h
  2. customquenched with 70% acetic acid (2.4 mL) and water (4.0 mL)
  3. filtrationThe suspension was filtered
  4. washwashed with waterlethanol and water
  5. dry with materialdried over P2O5 under high vacuum

出典と根拠

ORDレコード
ord-79accb4e2e0c4db8b83d899b07c47d1d
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973051B2

反応ノート

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