Acetic Acid → methyl 5-[2-(2-chloroacetylamino)phenyl]-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1442544

Reaction equation

HRID 1442544 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][C:11]2[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=2[C:9]=1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:35][CH2:36][C:37](Cl)=[O:38]>O1CCCC1>[Cl:35][CH2:36][C:37]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][C:11]2[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:10]=2[C:9]=1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:38]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 58679076methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679064methyl 5-[2-(2-chloroacetylamino)phenyl]-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate obtained in Step 9, sodium acetate (2.4 g, 29 mmol) and acetic acid (1.7 ml, 29 mmol) in tetrahydrofuran (70 ml) was added chloroacetyl chloride (2.3 ml, 29 mmol) under ice-cooling. After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. Water (100 ml) was added to the obtained solid. The solid was collected by filtration, washed with diethyl ether (20 ml×2), and dried under reduced pressure to give methyl 5-[2-(2-chloroacetylamino)phenyl]-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (5 g, yield after 2 steps from Step 9: 58%).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater (100 ml) was added to the obtained solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with diethyl ether (20 ml×2)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-f8f0a2110275457a910afb39a95cb202
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Linked notes

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