Chloral Hydrate → HCID 20829800, compound

HRID 496598Notes

Reaction equation

HRID 496598 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[CH:3](O)[OH:4].[CH:8]1([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C1C=CC=CC=1>[CH:8]1([C:14]([NH:16][CH:3]([OH:4])[C:2]([Cl:7])([Cl:6])[Cl:1])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 2707Chloral HydrateHCID 14283Cyclohexanecarboxamide

Product 1

HCID 20829800HCID 20829800, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

First, cyclohexyl-N-(2,2,2-trichloro-1-hydroxyethyl)carboxamide 3 was synthesized as follows. A mixture of chloral hydrate (9.0 g, 54,5 mmol) and cyclohexane carboxamide (5.0 g, 49.5 mmol) in dry benzene (30 ml) was heated at 80° C. in an oil bath. The initial suspension eventually became a clear solution (reaction time depends on the amount of starting materials, in this example it took about 6 hours). The mixture was stirred for an additional 30 minutes, then removed from the oil bath, and left at room temperature. Upon cooling, the crystalline solid formed was filtered and washed with hexanes to give the product cyclohexyl-N-(2,2,2-trichloro-1-hydroxyethyl)carboxamide 3 (11.0 g). NMR (1H, CDCl3): δ 6.23 (d, J=8.4 Hz, 1H), 5.9 (dd, 1H), 4.35 (broad s, 1H), 2.16 (t, 1H), 1.90-1.22 (m, 10H).

Workup

  1. customFirst, cyclohexyl-N-(2,2,2-trichloro-1-hydroxyethyl)carboxamide 3 was synthesized
  2. customreaction time
  3. customremoved from the oil bath
  4. waitleft at room temperature
  5. temperatureUpon cooling
  6. customthe crystalline solid formed
  7. filtrationwas filtered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-9c98bbfa8e2c43289cef07d41ded29a0
Source dataset
uspto-grants-2005_09
Patent number
US06946474B2

Reaction notes

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