4-amino-N-(bis-methylsulfanyl-methylene)benzenesulfonamide → 4-Amino-N-[(8-benzyl-2,3,8-triaza-spiro[4.5]dec-3-en-2-yl)-methylsulfanyl-methylene]-benzenesulfonamide

HRID 1044687Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([S:15][CH3:16])SC)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:17]([N:24]1[CH2:33][CH2:32][C:27]2([CH2:31][N:30]=[N:29][CH2:28]2)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]=[C:12]([N:30]2[N:29]=[CH:28][C:27]3([CH2:32][CH2:33][N:24]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:25][CH2:26]3)[CH2:31]2)[S:15][CH3:16])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

In a 25 mL microwave vial, 1.50 g 4-amino-N-(bis-methylsulfanyl-methylene)benzene-sulfonamide and 1.37 g 8-benzyl-2,3,8-triaza-spiro[4.5]dec-2-ene were suspended in 20 mL pyridine. The vial was capped and heated for 1 hour at 180° C. (6 bar) in the microwave. The reaction mixture was concentrated on silica. Purification with flash column chromatography (DCM→DCM/MeOH 99:1→DCM/MeOH 98:2) yielded 1.03 g (41%) of a beige amorph. 1H NMR (400 MHz, CDCl3) δ 1.57-1.72 (m, 2H), 1.78-1.92 (m, 2H), 2.17-2.32 (m, 5H), 2.66-2.81 (m, 2H), 3.51 (s, 2H), 4.04 (s, 2H), 4.28 (s, 2H), 6.64-6.71 (m, 2H), 6.98 (s, 1H), 7.20-7.37 (m, 5H), 7.72-7.79 (m, 2H).

Workup

customThe vial was capped
concentrationThe reaction mixture was concentrated on silica
customPurification with flash column chromatography (DCM→DCM/MeOH 99:1→DCM/MeOH 98:2)
customyielded 1.03 g (41%) of a beige amorph

Sources & evidence

ORD record: ord-dc45f8c2c90a49488f792d3bca34d96e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563723B2

Reaction notes

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