Benzoyl isothiocyanate → HCID 10414012, compound

HRID 723964Notes

Reaction equation

HRID 723964 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:4][CH:3]=1.[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1.C(Cl)Cl>[C:21]([NH:29][C:30]([NH:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([NH:10][CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[S:12][C:13]=2[CH:19]=1)=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 21878492HCID 21878492, compound

Product 1

HCID 10414012HCID 10414012, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N2-[2-(4-Bromo-phenyl)-ethyl]-benzothiazole-2,6-diamine (Example 33(a), 71 mg, 0.205 mmol) was dissolved in tetrahydrofuran (3 mL). Benzoyl isothiocyanate (20 μl, 1.1 eq) was added and the mixture stirred at room temperature for 24 hours. The solvent was evaporated to give a yellow solid. The solid was dissolved in CH2Cl2 (5 mL) and absorbed onto silica gel. The absorbed compound was loaded onto a silica column and eluted with a mixture of ethyl acetate/hexanes (1:1) to give a yellow solid (99 mg, 95%). 1H NMR (CDCl3) δ: 12.61 (s, 1H), 9.10 (s, 1H), 8.19 (s, 1H), 7.90 (d, 2H, J=8.5 Hz), 7.67–7.43 (m, 8H), 7.12 (d, 2H, J=8.5 Hz), 3.69 (t, 2H, J=6.9 Hz), 2.97 (d, 2H, J=6.9 Hz).

Workup

  1. customThe solvent was evaporated
  2. customto give a yellow solid
  3. customabsorbed onto silica gel
  4. washeluted with a mixture of ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-7239a82f1ad34d478a1cb85d7a0ab09d
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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