1-Isocyanato-3,5-dimethoxybenzene → HCID 178444872, compound

HRID 2240325Notes

Reaction equation

HRID 2240325 reaction equation
[CH2:1]([NH:7][C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[C:13]([SH:15])[S:14][C:10]=2[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([N:28]=[C:29]=[O:30])[CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1>ClCCl>[CH3:27][O:26][C:24]1[CH:23]=[C:22]([NH:28][C:29](=[O:30])[N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([SH:15])[S:14][C:10]=3[CH:9]=2)[CH:21]=[C:20]([O:19][CH3:18])[CH:25]=1

Participants

4

Reactant 2

HCID 27362001-Isocyanato-3,5-dimethoxybenzeneHCID 178444737HCID 178444737, compound

Product 1

HCID 178444872HCID 178444872, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 50 ml round bottomed flask were added 6-(hexylamino)-1,3-benzothiazole-2-thiol (58.5 mg, 0.22 mmol), dichloromethane (10 ml) and 3,5-dimethoxyphenyl isocyanate (39.5 mg, 0.22 mmol). The reaction mixture was stirred 8 h, filtered, and the solid that was obtained was triturated with chloroform, followed with chloroform/methanol (9:1 mixture) to give 42 mg (43%) of the title compound. 1H NMR (DMSO-d6) δ=0.79 (t, 3H), 1.19 (br s, 5H), 1.40 (t, 2H), 3.28 (br s, 2H), 3.57 (t, 2H), 3.61 (s, 5H), 6.65 (d, 1H), 7.20 (d, 2H), 7.28 (d, 1H), 7.61 (d, 1H), 7.67 (s, 1H); ESIMS: m/z 444 (M−H).

Workup

  1. filtrationfiltered
  2. customthe solid that was obtained
  3. customwas triturated with chloroform

Sources & evidence

ORD record
ord-e06652737e4248d5b0259b7eecbd0cec
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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