Carbamic Acid → HCID 86618659, compound

HRID 1644132Notes

Reaction equation

HRID 1644132 reaction equation
ClC[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH2:12]([N:14]([CH2:18][CH3:19])[C:15](=[S:17])[SH:16])[CH3:13].[Na].[C:21](=O)(O)N>C(O)C>[CH2:12]([N:14]([CH2:18][CH3:19])[C:15]([S:16][CH2:21][C:6]1([CH:5]=[CH:4][CH:3]=[CH:11][CH2:10]1)[C:7]([OH:9])=[O:8])=[S:17])[CH3:13]

Participants

6

Reactant 4

HCID 277Carbamic AcidHCID 8987DitiocarbHCID 742344-(Chloromethyl)benzoic acidHCID 5360545Sodium

Product 1

HCID 86618659HCID 86618659, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
45 °C

Procedure

4-Chloromethylbenzoic acid (4 g, 0.0234 mol, 1.0 equiv.) was dissolved in warm ethanol (20 mL). Diethyldithiocarbamic acid, sodium salt trihydrate (7.92 g, 0.0328 mol, 1.5 equiv.) was also separately dissolved in warm ethanol (20 mL). The solution of the carbamic acid was then added to the solution of the carboxylic acid. The resulting mixture was then stirred at 40-50° C. for 2 h, then stirred overnight at r.t. The reaction mixture was then evaporated to dryness and separated between dichloromethane and brine. The aqueous layer was separated and acidified with conc. HCl to a pH value of 2. The precipitate that formed on acidification was filtered and air-dried to give a white solid, 4.1 g (yield 62%). 1H NMR (acetone-d6, 400 MHz) δ 1.26, br.s, 6H, 2×CH3; 3.82, br.s, 2H, CH2N; 4.5, br.s, 2H, CH2N; 4.67, s, 2H, CH2S; 7.56 (d, J=8 Hz, 2H, aromatic); 7.98 (d, J=8 Hz, 2H, aromatic) ppm. 13C NMR (acetone-d6, 400 MHz) δ 11.78, 12.98, 41.53, 47.55, 50.45, 130.26, 130.45, 130.69, 143.74, 167.40, 194.94 ppm.

Workup

  1. stirringstirred overnight at r.t
  2. customThe reaction mixture was then evaporated to dryness
  3. customseparated between dichloromethane and brine
  4. customThe aqueous layer was separated
  5. customThe precipitate that formed on acidification
  6. filtrationwas filtered
  7. customair-dried
  8. customto give a white solid, 4.1 g (yield 62%)

Sources & evidence

ORD record
ord-410feb6d50224b7ababab615e79dab68
Source dataset
uspto-grants-2012_02
Patent number
US08124188B2

Reaction notes

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