Ammonia → (S)-1-[1-(thiophen-2-ylthiazol-4-yl)-2-(4-nitrophenyl)ethyl]-thiourea

HRID 1046618Notes

Reaction equation

HRID 1046618 reaction equation
Br.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@@H:12]([C:14]2[N:15]=[C:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[S:17][CH:18]=2)[NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].C([O-])([O-])=O.[Ca+2].[C:29](Cl)(Cl)=[S:30].[NH3:33]>C(Cl)(Cl)(Cl)Cl.O.C(Cl)Cl.O>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:16]1[S:17][CH:18]=[C:14]([C@@H:12]([NH:13][C:29]([NH2:33])=[S:30])[CH2:11][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)[N:15]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 66704718(S)-2-(4-nitrophenyl)-1-(thiophen-2-ylthiazol-4-yl)ethanamine hydrobromide salt

Product 1

HCID 59464673(S)-1-[1-(thiophen-2-ylthiazol-4-yl)-2-(4-nitrophenyl)ethyl]-thiourea

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 17768942Tetrachloromethane--water (1/1)Solvent

Procedure

To a solution of (S)-2-(4-nitrophenyl)-1-(thiophen-2-ylthiazol-4-yl)ethanamine hydrobromide salt, 8, (1.23 g, 2.98 mmol) and CaCO3 (0.597 g, 5.96 mmol) in CCl4/water (10 mL/5 mL) is added thiophosgene (0.412 g, 3.58 mmol). The reaction is stirred at room temperature for 18 hours then diluted with CH2Cl2 and water. The layers are separated and the aqueous layer extracted with CH2Cl2. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated in vacuo to a residue which is subsequently treated with ammonia (0.5M in 1,4-dioxane, 29.4 mL, 14.7 mmol) which is purified over silica to afford 0.490 g of the desired product as a red-brown solid. ESI+MS 399 (M+1).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer extracted with CH2Cl2
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo to a residue which
  6. customis purified over silica

Sources & evidence

ORD record
ord-bc339828035b494f91b3b5391710f1b3
Source dataset
uspto-grants-2013_10
Patent number
US08569348B2

Reaction notes

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