Thiophosgene → HCID 89765672, compound

HRID 2272989Notes

Reaction equation

HRID 2272989 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 is added dropwise and stirred for 20 minutes. When the reaction is completed, the reaction mixture is 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 is concentrated at room temperature
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-3971fb103ff34ea984b72d1816b6a925
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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