Benzylamine → 2-Benzylamino-5-nitro-benzenesulfonamide

HRID 884202Notes

Reaction equation

HRID 884202 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
92 °C

Procedure

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%).

Workup

  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.

Sources & evidence

ORD record
ord-8a14744508b3438e842279492cf3d6de
Source dataset
uspto-grants-2012_08
Patent number
US08236948B2

Reaction notes

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