Dimethylamine → 1,1-Dimethyl-3-(5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-urea

HRID 595085Notes

Reaction equation

HRID 595085 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH:8]([CH3:12])[CH2:7][C:5]=2[N:6]=1.C1CCN2C(=NCCC2)CC1.C1N=[CH:27][N:26]([C:29](N2C=NC=C2)=[O:30])[CH:25]=1.CNC>CC#N>[CH3:25][N:26]([CH3:27])[C:29]([NH:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH:8]([CH3:12])[CH2:7][C:5]=2[N:6]=1)=[O:30]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 27565102-Amino-5-methyl-4,5,6-trihydrobenzothiazol-7-one

Product 1

HCID 866646061,1-Dimethyl-3-(5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-ureaYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-amino-5-methyl-5,6-dihydro-4H-benzothiazol-7-one (30.0 g, 0.165 mol) in MeCN (750 mL) are added DBU (75.2 g, 0.495 mol) and CDI (80.1 g, 0.495 mol) at RT. The reaction mixture is stirred at 110° C. overnight. Dimethylamine (93.5 g, 1.15 mol) and another portion of DBU (175 g, 1.15 mol) are added to the mixture at RT and the stirring is continued overnight at 110° C. After cooling to RT, the reaction mixture is evaporated in vacuo and the residue is poured into ice water. The reaction mixture is treated with HCl (6 M) to pH to 5. The aqueous mixture is extracted with EtOAc (3×300 mL). The combined organic phase is washed with brine and dried over anhydrous Na2SO4. The solvent is evaporated and the residue is recrystallized from hexane to give 1,1-dimethyl-3-(5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-urea (32.1 g, 77% yield).

Workup

  1. waitthe stirring is continued overnight at 110° C
  2. temperatureAfter cooling to RT
  3. customthe reaction mixture is evaporated in vacuo
  4. additionthe residue is poured into ice water
  5. additionThe reaction mixture is treated with HCl (6 M)
  6. extractionThe aqueous mixture is extracted with EtOAc (3×300 mL)
  7. washThe combined organic phase is washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent is evaporated
  10. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-9322ab1795cb4f8790bf1c09d6a1b122
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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