Thiophosgene → HCID 89765672, compound

HRID 570596Notes

Reaction equation

HRID 570596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:15])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH2:11][CH2:12][N:13]=1.C(N(C(C)C)CC)(C)C.[C:25](Cl)(Cl)=[S:26]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:15]=[C:25]=[S:26])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH2:11][CH2:12][N:13]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 81531DiisopropylethylamineHCID 66583483HCID 66583483, compound

Product 1

HCID 89765672HCID 89765672, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-chloro-4-(1-methyl-4,5-dihydro-1H-imidazol-2-ylsulfanyl)-phenylamine (5.0 g, 21 mmol) and diisopropylethylamine (5.37 g, 41.6 mmol) in dry tetrahydrofuran at 0° C. under N2 inert atmosphere, thiophosgene (2.39 g, 21 mmol) in tetrahydrofuran was added dropwise and stirred for 20 minutes. When the reaction was completed, the reaction mixture was concentrated at room temperature and taken in dichloromethane (100 mL), washed with water (2×50 mL) and dried over anhydrous MgSO4 to get the product as a brown solid (5.8 g, 99%). TLC: pet ether/ethyl acetate (8/2) Rf-0.4. LCMS (method A): mass found (M+H+, 282.0), Rt (min): 3.43, area % 71.5 (max); 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=2.16 Hz, 1H), 7.57 (s, 1H), 7.31 (m, 1H), 7.28 (m, 1H), 6.43 (d, J=8.56 Hz, 1H), 3.61 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated at room temperature
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-9ee9f885743748108fdaa1abab905ade
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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