P-Anisidine → HCID 86749818, compound

HRID 743492Notes

Reaction equation

HRID 743492 reaction equation
[CH3:1][O:2][C:3]1[CH:42]=[CH:41][C:6]([CH2:7][S:8][C:9]([CH3:40])([CH3:39])[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:34][CH2:35][N:36]=[C:37]=[S:38])[CH2:16][CH2:17][NH:18][C:19](=[O:33])[C:20]([CH3:32])([S:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH3:21])=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][CH:53]=1>C(Cl)(Cl)Cl>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][S:22][C:20]([CH3:32])([CH3:21])[C:19]([NH:18][CH2:17][CH2:16][N:15]([CH2:34][CH2:35][NH:36][C:37]([NH:58][C:55]2[CH:56]=[CH:57][C:52]([O:51][CH3:50])=[CH:53][CH:54]=2)=[S:38])[CH2:14][CH2:13][NH:12][C:10](=[O:11])[C:9]([CH3:40])([S:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:42][CH:41]=2)[CH3:39])=[O:33])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 86749817HCID 86749817, compound

Product 1

HCID 86749818HCID 86749818, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the isothiocyanate 25 (18.9 mg, 0.02986 mmol), triethylamine (7.26 mg, 0.07175 mmol), anisidine (6.9 mg, 0.05602 mmol), and CHCl3 (15 mL) was refluxed for 3 hours and the solvent was removed in vacuo. Flash chromatography of this crude product using 100% EtOAc gave the anisidine derivative 26 as a clear oil (19.8 mg, 87.6% yield). 1H NMR (in CDCl3): δ8.17 (brs,lH,NH--CS--NH--Ar), 7.28 (d,j=8.8 Hz,2H,H2 &H6 --Ar--N), 7.15 (d,j=8.6 Hz,4H,2H3 &H5 --Ar--OCH3), 7.06 (brs,lH,NH--CS--NH--Ar), 7.06 (t,j=5.7 Hz,2H,2NH--CO), 6.90 (d,j=8.9 Hz,2H,H3 &H5 --Ar--N), 6.82 (d,j=8.6 Hz,4H,2H2 &H6 --Ar--OCH3), 3.79 (s,3H,CH3O--Ar--N), 3.77 (s,6H,2CH3O--Ar--CH2), 3.67 (s,4H,2S--CH2 -Ar), 3.61 (q,j=5.3 Hz,2H,N--CH2CH2 --NHCS), 3.14 (q,j=6.2 Hz,4H,2N-CH 2CH2 --NHCO), 2.69 (t,j=5.6 Hz,2H,N--CH2CH2 --NHCS), 2.52 (t,j=6.3Hz,4H 2N--CH2CH2 --NH--CO), 1.51 (br s,12H,4CH3 --C--S) ppm. 13C NMR (in CDCl3): δ181.9 (s,N--CS--N), 175.2 (s,2NH--CO), 158.8 (s,3C1 --Ar--OCH3), 130.0 (s,C1 --Ar--N), 130.0 (d,2C2 &C6 --Ar--OCH3), 129.2 (s,2C4 --Ar--OCH3), 127.0 (d,C2 &C6 --Ar--N), 114.5 (d,C3 &C5 --Ar--N), 114.2 (d,2C3 &C5 --Ar--OCH3), 55.4 (q,3CH3O), 54.4 (t,2N-CH 2CH2 --NHCO), 52.9 (t,N--CH2CH2 --NHCS), 50.1 (s,2S--C--CH3), 42.8 (t,N--CH2CH2 --NHCS), 38.3 (t,2N--CH2CH2 --NHCO), 34.2 (t,2S--CH2 --Ar), 28.3 (q,4CH3 --C--S) ppm. MS (m/z,FAB): 756(4.2, M+). IR (CDCl3): 3320, 2960, 1720, 1655, 1510, 1290, 1245, 1030 cm-1.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1d72ceee6999449db68b45596af6ea56
Source dataset
uspto-grants-1996_09
Patent number
US05556939

Reaction notes

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