Chloroacetyl chloride → Acetanilide, 2-chloro-4'-nitro-

HRID 716858

反応式

HRID 716858 の反応式
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][CH2:12][C:13](Cl)=[O:14]>C1COCC1>[Cl:11][CH2:12][C:13]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:14]

参加物

4

反応物 2

HCID 6577Chloroacetyl chlorideHCID 74754-Nitroaniline

生成物 1

HCID 140220Acetanilide, 2-chloro-4'-nitro-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-nitroaniline 37b (6.9 g, 50 mmol) in THF (50 mL) was added dropwise a solution of chloroacetyl chloride (100 mmol) in dry THF (50 mL) at room temperature. The reaction mixture was stirred for additional 40-45 minutes and then evaporated in vacuo to dryness. The solid residue was triturated with saturated NaHCO3 solution (aqueous) and then collected by filtration. The solid product was washed with water, followed by hexane, and dried to give 2-chloro-N-(4-nitrophenyl)acetamide, 10.02 g (94%); mp 182-183° C. (Lit. 181-183° C.58). 1H NMR (DMSO-d6) δ: 4.34 (2H, s, CH2), 7.83-7.85 (2H, d, J=9.1 Hz, Ar—H), 8.23-8.26 (2H, d, J=9.1 Hz, Ar—H), 10.88 (1H, brs, NH).

後処理

  1. customevaporated in vacuo to dryness
  2. customThe solid residue was triturated with saturated NaHCO3 solution (aqueous)
  3. filtrationcollected by filtration
  4. washThe solid product was washed with water
  5. customdried

出典と根拠

ORDレコード
ord-c799ec5f684d40ff855dd6407a630b64
出典データセット
uspto-grants-2015_11
特許番号
US09193687B2

関連ノート

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