1,2-dichloro-4-[(3,4-dichlorophenyl)disulfanyl]benzene → HCID 71625513, compound

HRID 589617Notes

Reaction equation

HRID 589617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1.[Cl:22]C1C=C(SSC2C=CC(Cl)=C(Cl)C=2)C=CC=1Cl>>[Cl:22][C:7]1[CH:6]=[C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:19]([OH:21])=[O:20])[CH:4]=[CH:3][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 6010601,2-dichloro-4-[(3,4-dichlorophenyl)disulfanyl]benzeneHCID 6623329HCID 6623329, compound

Product 1

HCID 71625513HCID 71625513, compoundYield 43.4%

Procedure

Following the method used to prepare 1, product 1 (0.15 g, 0.85 mmol) and bis(3,4-dichlorophenyl)disulfide (66) (0.37 g, 1.03 mmol) provided 0.13 g of product 21 (43%) as an off white solid, mp 252-255° C. 1H NMR (300 MHz, DMSO-d6) δ 2.40 (s, 3H), 6.95 (dd, J=2, 9 Hz, 1H), 6.99 (d, J=9 Hz, 1H), 7.23 (d, J=2 Hz, 1H), 7.30-7.34 (m, 2H), 7.46 (d, J=9 Hz, 1H), 12.30 (s, 1H), 13.38 (s, 1H). LC-MS (CI): m/z 350.0, 352.0 [(M−H)− C16H11Cl2NO2S requires 350.99]. Purity (100%). Calcd for C16H11Cl2NO2S.0.04-CH2Cl2: C, 54.17; H, 3.14; N, 3.94; S, 9.02; Cl, 20.74. Found: C, 54.00; H, 2.95; N, 3.93; S, 9.02; Cl, 20.74.

Sources & evidence

ORD record
ord-e6523d82bee44575974f558c31a1759b
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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