Triethylamine → 6-Methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4(3H)-one

HRID 540218Notes

Reaction equation

HRID 540218 reaction equation
Cl[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[S:14]1(=[O:25])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:17]1[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:14](=[O:25])[CH2:15][CH2:16]1)[NH:11][C:10]2=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 1355887902-Chloro-6-methyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 1363367986-Methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4(3H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-chloro-6-methylquinazolin-4(3H)-one (15 g, 77.3 mmol) and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide (16.8 g, 103 mmol) in toluene (200 mL) was added triethylamine (16.1 mL, 116 mmol). After being refluxed overnight, the reaction mixture was cooled to room temperature. The formed solid was collected by filtration, washed with ethanol (50 mL) and ethyl acetate (100 mL), and then dried in vacuo to afford 21.0 g of the desired product as a white solid (yield was 80%).

Workup

  1. temperatureAfter being refluxed overnight
  2. filtrationThe formed solid was collected by filtration
  3. washwashed with ethanol (50 mL) and ethyl acetate (100 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-59da41b5036a4b53a61f068805f8a67a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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