Dimethylamine → HCID 86653428, compound

HRID 1874070Notes

Reaction equation

HRID 1874070 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.C1CCN2C(=NCCC2)CC1.C1N=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1.CNC>C(#N)C>[CH3:24][N:25]([CH3:26])[C:28]([NH:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1)=[O:29]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Product 1

HCID 86653428HCID 86653428, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (10 g, 59 mmol), DBU (18 mL, 0.12 mol) and CDI (24 g, 0.15 mol) in 400 mL acetonitrile is stirred for 5 h at 100° C. Then dimethylamine (150 mL, 2M in THF) is added and the reaction mixture is stirred overnight at 100° C. The reaction mixture is concentrated under reduced pressure and the residue is poured in water. The mixture is acidified to pH 5 with 6 M HCl in water and extracted with ethyl acetate. The combined organic phases are dried over MgSO4 and concentrated under reduced pressure. The residue is triturated with diethyl ether. Yield: 9.1 g.

Workup

  1. stirringthe reaction mixture is stirred overnight at 100° C
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is poured in water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-b25ff7917f834e4fbec0d38ecf05c7ea
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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