Dichloromethane → 1-(Methoxycarbonyl)propyl 4-(hexadecylamino)-2-thiophenecarboxylate

HRID 850984Notes

Reaction equation

HRID 850984 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24](Cl)=[O:25])[S:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(Cl)Cl.[OH:30][CH:31]([CH2:36][CH3:37])[C:32]([O:34][CH3:35])=[O:33].C(N(CC)CC)C>CCOCC>[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24]([O:30][CH:31]([C:32]([O:34][CH3:35])=[O:33])[CH2:36][CH3:37])=[O:25])[S:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 520445Methyl 2-hydroxybutanoateHCID 205036504-Hexadecylamino-2-thiophenecarbonyl chloride hydrochloride

Product 1

HCID 205036411-(Methoxycarbonyl)propyl 4-(hexadecylamino)-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10 g. of 4-hexadecylamino-2-thiophenecarbonyl chloride hydrochloride in 200 ml. methylene chloride is added dropwise a solution of 3 g. methyl α-hydroxybutyrate and 5 g. triethylamine in 100 ml. ether. After 17 hours stirring at room temperature, the precipitate is collected and washed with several protions of ether. The ether solution is washed with water, dried and evaporated to yield 1-(methoxycarbonyl)propyl 4-(hexadecylamino)-2-thiophenecarboxylate as a white solid.

Workup

  1. customthe precipitate is collected
  2. washwashed with several protions of ether
  3. washThe ether solution is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4d1da3e48c3344e593357643f51c242e
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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