Thiophosgene → HCID 86749817, compound

HRID 743491Notes

Reaction equation

HRID 743491 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][S:8][C:9]([CH3:38])([CH3:37])[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:34][CH2:35][NH2:36])[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:41](Cl)(Cl)=[S:42]>ClCCl>[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][S:8][C:9]([CH3:38])([CH3:37])[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:34][CH2:35][N:36]=[C:41]=[S:42])[CH2:16][CH2:17][NH:18][C:19](=[O:33])[C:20]([CH3:32])([S:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[CH3:21])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 69827959HCID 69827959, compound

Product 1

HCID 86749817HCID 86749817, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round bottom flask containing the aniline 24 (28.8 mg, 0.0487 mmol) and dichloromethane (10 mL) was added 0.2211 M solution of thiophosgene (0.22 mL, 0.0509 mmol) in dichloromethane. The heterogeneous reaction mixture was stirred at room temperature for 1 hour and the solvent was removed in vacuo. Flash chromatography of this crude product using 100% EtOAc gave the isothiocyanate 25 as a clear oil (18.9 mg, 61.3% yield). 1H NMR (in CDCl3): δ7.17 (d,j=8.5 Hz,4H,2H3 &H5 --Ar--OCH3), 7.07 (m,2H,2NH--CO), 6.82 (d,j=8.5 Hz,4H,2H2 &H6 --Ar--OCH3), 3.78 (s,6H, 2CH3O), 3.70 (s,4H,2S--CH2 --Ar), 3.49 (t,j=5.9 Hz,2H,N--CH2CH2 -NCS ), 3.21 (q,j=6.2 Hz,4H,2N--CH2CH2 --NHCO), 2.78 (t,j=5.9 Hz,2H,N--CH2CH2 --NCS), 2.58 (t,j=6.4 Hz,4H, 2N--CH2CH2 --NHCO), 1.54 (s,12H,4CH3 --C--S) ppm. MS (m/z,CI): 633(25, MH+). IR (CDCl3): 3370, 2950, 2920, 2850, 2100, 1720, 1655, 1610, 1510, 1245, 1170, 1030, 830 cm-1.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ff02ac5a4fe24466963b3b84efacc699
Source dataset
uspto-grants-1996_09
Patent number
US05556939

Reaction notes

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