Thiourea → 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-2-thiol

HRID 464176Notes

Reaction equation

HRID 464176 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[NH2:25][C:26]([NH2:28])=[S:27].C[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:28]=[C:26]([SH:27])[N:25]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 536569248-Chloro-1-(2-chlorophenyl)-4-dimethylaminomethylidene-3,4-dihydro-2-benzazepin-5-one

Product 1

HCID 1785278489-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-2-thiol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 2.8 g (7.8 mmole) of 8-chloro-1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 2.8 g (37 mmole) of thiourea, and 8.0 ml (32 mmole) of a 4.0M methanol solution of sodium methoxide in 80 ml of methanol was stirred at room temperature for 18 hr. The mixture was diluted with water and extracted with ether. The aqueous layer was neutralized with acetic acid and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow solid, mp 238°-239° C. Recrystallization from tetrahydrofuran gave yellow crystals, mp 232°-234° C.

Workup

  1. extractionextracted with ether
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto give a yellow solid, mp 238°-239° C
  6. customRecrystallization from tetrahydrofuran
  7. customgave yellow crystals, mp 232°-234° C.

Sources & evidence

ORD record
ord-65afc291998e422cbff7893a0fa39e73
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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