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

HRID 716858

반응식

HRID 716858 반응식
[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]

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 74754-Nitroaniline

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c799ec5f684d40ff855dd6407a630b64
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193687B2

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