Triethylamine → HCID 13061696, compound

HRID 1703185Notes

Reaction equation

HRID 1703185 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[C:8]([O:17][CH3:18])[C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:4]=1.C(N(CC)CC)C.Cl[C:33]1[S:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1>C(O)CCC>[S:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[N:22]1[CH2:23][CH2:24][N:19]([C:5]2[N:4]=[C:3]([NH2:2])[C:12]3[C:7](=[C:8]([O:17][CH3:18])[C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119872-ChlorobenzothiazoleHCID 20523604HCID 20523604, compound

Product 1

HCID 13061696HCID 13061696, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-amino-2-(1-piperazinyl)-6,7,8-trimethoxyquinazoline hydrochloride (4.0 g) and triethylamine (4.1 g) in butanol (250 ml) was stirred for 15 min and 2-chlorobenzthiazole (1.7 g) was added. The resulting mixture was refluxed for 20 hr, concentrated to about 150 ml, cooled and filtered. The precipitate was washed with water, dried and crystallized from methanol to give the title compound (2.2 g): mp>250° C.; ir (nujol) 3370, 3300 and 3610 cm-1 ; uv max (MeOH) 225 (ε=45,900), 250 (ε=56,700), 277 (ε=45,200) and 353 nm (ε=5,100); nmr (DMSO-d6) δ3.7 (m, 8H), 3.8 (s, 6H), 3.95 (s, 3H) and 7.3 (m, 7H); and Anal. Calcd. for C22H24N6O3S: C, 58.40% H, 5.30% N, 18.58% and Found: C, 58.22% H, 5.50% N, 18.62%.

Workup

  1. temperatureThe resulting mixture was refluxed for 20 hr
  2. concentrationconcentrated to about 150 ml
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe precipitate was washed with water
  6. customdried
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-438bb14b6a2d480bbeb088e9ca6f842a
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

Loading…