Acetic acid, 2-isothiocyanato-, ethyl ester → HCID 135849830, compound

HRID 1042226Notes

Reaction equation

HRID 1042226 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]2=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[N:31]([CH2:34][C:35]([O:37]CC)=[O:36])=[C:32]=[S:33]>C(Cl)(Cl)Cl>[CH:1]1([N:7]2[C:12]([OH:13])=[C:11]([C:32]([NH:31][CH2:34][C:35]([OH:37])=[O:36])=[S:33])[C:10](=[O:14])[N:9]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[C:8]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 32202Acetic acid, 2-isothiocyanato-, ethyl esterHCID 372731,3-Dicyclohexyl-1,3-diazinane-2,4,6-trioneHCID 81531Diisopropylethylamine

Product 1

HCID 135849830HCID 135849830, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1,3-dicyclohexyl-2,4,6(1H,3H,5H)-pyrimidinetrione (660 mg, 2.25 mmoles), diisopropylethylamine (780 uL, 4.5 mmoles) and ethyl isothiocyanatoacetate (340 uL, 2.75 mmoles) in chloroform (20 mL) was stirred overnight. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The solid residue was purified by flash chromatography (dichloromethane) and the fractions evaporated, dissolved in ethanol (5 mL, some heating) and treated with 1 molar sodium hydroxide (3 mL). The mixture was stirred for 30 minutes and acidified to give a solid which recrystallized from ethanol-water to give the title compound (135 mg, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.16 (s, 1 H), 12.54 (t, J=4.80 Hz, 1 H), 4.69 (t, J=12.00 Hz, 2 H), 4.35 (d, J=5.05 Hz, 2 H), 2.25 (q, 4 H), 1.79 (d, J=12.38 Hz, 4 H), 1.63 (d, J=12.38 Hz, 6 H), 1.29 (q, 4 H), 1.13 (q, 2 H).

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customdried
  3. customevaporated
  4. customThe solid residue was purified by flash chromatography (dichloromethane)
  5. customthe fractions evaporated
  6. dissolutiondissolved in ethanol (5 mL
  7. additionsome heating) and treated with 1 molar sodium hydroxide (3 mL)
  8. stirringThe mixture was stirred for 30 minutes
  9. customto give a solid which
  10. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-0818cb1c516e4a5b9befd9bc92be3202
Source dataset
uspto-grants-2013_10
Patent number
US08557834B2

Reaction notes

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