Benzylamine → 2-Benzylamino-5-nitro-benzenesulfonamide

HRID 548285노트

반응식

HRID 548285 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C>[CH2:15]([NH:22][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 667842-Chloro-5-nitrobenzenesulfonamide

생성물 1

HCID 248583972-Benzylamino-5-nitro-benzenesulfonamide수율 84%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
92 °C

실험 절차

A mixture of 2-chloro-5-nitro-benzenesulfonamide (2.20 kg, 9.30 mol), benzylamine (1.5 L, 13.9 mol), triethylamine (2.5 L, 18.1 mol), and acetonitrile (22.0 L) were heated at 92° C. for 20 h. The mixture was then cooled to 40° C., and was then partially concentrated in vacuo. The residue was added to 0° C. water (22.0 L) and the resulting suspension was allowed to warm to 23° C. and stirred for 2 h. The suspension was filtered and the solid was then washed with water (5 L). The washed solid was suspended in absolute ethanol (11 L), and was then filtered and washed with absolute ethanol (5 L). The solid was further dried in vacuo at 45° C. to afford the desired product, 2-benzylamino-5-nitro-benzenesulfonamide (2.40 kg, 7.81 mol, 84%), as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 4.64 (2H, d, J=4.6 Hz), 6.81 (1H, d, J=9.4 Hz), 7.23-7.44 (6H, m), 7.77 (2H, bs), 8.11 (1H, dd, J1=9.4 Hz, J2=2.3 Hz), 8.49 (1H, d, J=3.1 Hz). LC-MS (ESI) calcd for C13H13N3O4S 307.06, found 308.2 [M+H+] (100%), 615.2 [2M+H+] (81%).

후처리

  1. temperatureThe mixture was then cooled to 40° C.
  2. concentrationwas then partially concentrated in vacuo
  3. additionThe residue was added to 0° C. water (22.0 L)
  4. temperatureto warm to 23° C.
  5. filtrationThe suspension was filtered
  6. washthe solid was then washed with water (5 L)
  7. filtrationwas then filtered
  8. washwashed with absolute ethanol (5 L)
  9. customThe solid was further dried in vacuo at 45° C.

출처 및 근거

ORD 기록
ord-4c9f2f9aea774250aeda9e358304960e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939524B2

반응 노트

불러오는 중…