Hydrochloric Acid → 2-(3-Chloropropanamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

HRID 1162749Notes

Reaction equation

HRID 1162749 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12].C(N(CC)CC)C.[Cl:21][CH2:22][CH2:23][C:24](Cl)=[O:25].Cl>C(Cl)Cl>[Cl:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 2902232-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

Product 1

HCID 16663982-(3-Chloropropanamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (250 mg, 1.28 mmol) and triethylamine (0.18 mL, 1.28 mmol) were stirred in DCM (5 mL). 3-chloropropionylchloride (162 mg, 1.28 mmol) was added dropwise under a nitrogen atmosphere. Stirring was continued for 2 h. 2 M HCl (20 mL) was added and the reaction mixture extracted into DCM (3×50 mL). The combined DCM layers were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to give the desired product as a yellow solid (290 mg, 1.01 mmol, 79%).

Workup

  1. extractionthe reaction mixture extracted into DCM (3×50 mL)
  2. washThe combined DCM layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f70242c89c05436b9e66bb60bcd8a260
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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