Triethylamine → HCID 68682013, compound

HRID 1865476Notes

Reaction equation

HRID 1865476 reaction equation
[CH:1]1([CH2:4][C:5]2([CH:16]([NH2:18])[CH3:17])[CH2:10][CH2:9][CH:8]([S:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].C(N(CC)CC)C>ClCCl>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22]([NH:18][CH:16]([C:5]1([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:6][CH2:7][CH:8]([S:11][CH2:12][CH:13]2[CH2:14][CH2:15]2)[CH2:9][CH2:10]1)[CH3:17])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 68682724HCID 68682724, compound

Product 1

HCID 68682013HCID 68682013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-{1-(cyclopropylmethyl)-4-[(cyclopropylmethyl)thio]cyclohexyl}ethyl)amine (0.1 g; 0.3745 mmol), 2,4-dichlorobenzoyl chloride (0.1174 g; 0.56175 mmol) and triethylamine (0.0567 g; 0.56175 mmol) were dissolved in dichloromethane and stirred for one hour at room temperature. The reaction was evaporated and partitioned between ethyl acetate and saturated bicarbonate solution. The organic layer was dried and evaporated and the residue was purified by silica chromatography using ethyl acetate hexanes to yield 2,4-dichloro-N-(1-{1-(cyclopropylmethyl)-4-[(cyclopropylmethyl)thio]cyclohexyl}ethyl) benzamide. (130 mg, 79%)

Workup

  1. customThe reaction was evaporated
  2. custompartitioned between ethyl acetate and saturated bicarbonate solution
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-92689d7f1ae443a8a5c5c1452eebbf61
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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