Carbon Disulfide → alpha-(Nitromethyl)benzyl 1-piperidinecarbodithioate

HRID 596497

Reaction equation

HRID 596497 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[N:12]1([C:18]([S-:20])=[S:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[NH2+]1CCCCC1.C(=S)=S>CO>[N:12]1([C:18]([S:20][CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[S:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 7626Beta-Nitrostyrene2×HCID 2820349Piperidinium 1-piperidinecarbodithioate

Product 1

HCID 11266906alpha-(Nitromethyl)benzyl 1-piperidinecarbodithioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
8 °C

Procedure

β-Nitrostyrene (14.9 grams, 0.10 mole) was added in portions to a stirred mixture of piperidinium 1-piperidinecarbodithioate (24.6 grams, 0.10 mole), and carbon disulfide (7.6 grams, 0.10 mole) in methanol (200 ml.). During the addition, the reaction temperature was 25° C.-29° C. After the addition of β-nitrostyrene, the reaction mixture was cooled to 8° C., and the precipitated product was filtered off, washed with water, and dried in air. The yield of product melting at 85° C.-87° C. (prior sintering) was 29.0 grams (93%). Repeated recrystallizations without heating from methylene chloride-hexane and methylene chloride-methanol solutions gave pure α-(nitromethyl)benzyl 1-piperidinecarbodithioate melting at 86° C.-90.5° C. (prior sintering).

Workup

  1. additionDuring the addition
  2. customwas 25° C.-29° C
  3. filtrationthe precipitated product was filtered off
  4. washwashed with water
  5. customdried in air
  6. customrecrystallizations
  7. temperaturewithout heating from methylene chloride-hexane and methylene chloride-methanol solutions

Sources & evidence

ORD record
ord-ae882f0193e946c4bdea7fcb06b2bf74
Source dataset
uspto-grants-1977_03
Patent number
US04011230

Linked notes

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