Dimethyl Sulfone → HCID 86681901, compound

HRID 1508369Notes

Reaction equation

HRID 1508369 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2([CH:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][CH2:21]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=O)=[CH:2]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30].CS(C)(=O)=O>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2([CH:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][CH2:21]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[S:30])=[CH:2]1

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 14817Phosphorus sulfide (P2S5)HCID 68155028HCID 68155028, compound

Product 1

HCID 86681901HCID 86681901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(1H-indol-3-yl)-3,3′-biindolin-2-one (728 mg, 2 mmol), crystalline P2S5.2 C5H5N (228 mg, 0.6 mmol) and dimethylsulfone (3.05 g) were heated (165-170° C.) for 20 min. The melt was allowed to cool and then heated in water for 10 min. The solid formed was collected, 766 mg (94%), mp>260° C. 1H NMR (300 MHz, DMSO-d6) δ 7.09-7.15 (m, 2H), 7.18-7.20 (m, 5H), 7.24-7.30 (m, 7H), 13.00 (s, 1H); 13C NMR (75.5 MHz, DMSO-d6) δ 72.7 (s), 111.2 (d), 124.4 (d), 126.5 (d), 127.5 (d), 128.6 (s), 128.7 (s), 129.0 (d), 129.1 (d), 129.1 (d), 139.2 (s), 143.0 (s), 143.5 (s), 145.3 (s, 2C), 208.4 (s). Elemental analysis calcd for C24H17N3S; C, 75.96; H, 4.51; N, 11.07. Found C, 76.10; H, 4.46; N, 11.00.

Workup

  1. temperatureto cool
  2. customThe solid formed
  3. customwas collected

Sources & evidence

ORD record
ord-0856c85917fa47b1bc0e2797f5b22aa2
Source dataset
uspto-grants-2015_12
Patent number
US09221855B2

Reaction notes

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