Carbon Disulfide → HCID 20155093, compound

HRID 364915Notes

Reaction equation

HRID 364915 reaction equation
[C:1](=S)=[S:2].[NH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[N:4]([CH2:5][CH2:6][CH2:7][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[S:15][C:16]2[C:21]1=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:1]=[S:2]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 11079240HCID 11079240, compound

Product 1

HCID 20155093HCID 20155093, compoundYield 124.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.2 g of carbon disulfide was added dropwise to a solution of 12.8 g of 10-(3-aminopropyl)phenothiazine and 7.7 ml of triethylamine in 100 ml of tetrahydrofuran. After stirring the solution at room temperature for 2 hours, a solution of 11.3 g of dicyclohexylcarbodiimide in 20 ml of tetrahydrofuran was added dropwise thereto, and the reaction was conducted at room temperature for 5 hours. After removing solvents in vacuo, 50 ml of ethyl acetate was added to the residue, and the crystals precipitated were collected by filtration, and the filtrate was concentrated to obtain 18.6 g of the desired compound (oily).

Workup

  1. waitthe reaction was conducted at room temperature for 5 hours
  2. customAfter removing solvents in vacuo, 50 ml of ethyl acetate
  3. additionwas added to the residue
  4. customthe crystals precipitated
  5. filtrationwere collected by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c05800596a9945af877d02afef2146f6
Source dataset
uspto-grants-1986_08
Patent number
US04607006

Reaction notes

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