Dichloromethane → 6-Amino-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole

HRID 723948Notes

Reaction equation

HRID 723948 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[S:10][C:6]=2[CH:5]=1)([O-])=O.Cl[Sn]Cl.N.CO.C(Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[S:10][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24479Stannous ChlorideHCID 21705897Ammonia methanolHCID 218784796-Nitro-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole

Product 1

HCID 218784956-Amino-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazoleYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-nitro-2-(2-pyrrolidin-1-ylethylamino)benzothiazole (Example 11, 50 mg, 0.17 mmol) and SnCl2 (161 mg, 0.85 mmol) in 20 mL of ethanol (denatured) was heated at reflux for 4 hours. After cooling the mixture was partitioned between 50 mL of ethyl acetate and 20 mL of 1.0N aqueous NaOH. The organic layer was dried over sodium sulfate and concentrated to give a yellow residue which was subjected to silica gel column chromatography (5% 2M NH3/MeOH:95% CH2Cl2). Yield: 65%, 1H-NMR (CD3OD): δ 8.70 (d, 1H, J=8.3 Hz); 8.47 (d, 1H, J=2.0 Hz); 8.21 (dd, 1H, J=6.3, 1.9 Hz); 5.05 (t, 2H, J=6.3 Hz); 4.28 (t, 2H, J=6.8 Hz); 4.14 (m, 4H); 3.33 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling the mixture
  4. customwas partitioned between 50 mL of ethyl acetate and 20 mL of 1.0N aqueous NaOH
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a yellow residue which

Sources & evidence

ORD record
ord-c0100381a0134bc3b306176718a1dc4e
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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