Triethylamine → Ro 11-7800

HRID 262985Notes

Reaction equation

HRID 262985 reaction equation
[Cl:1][C:2]1[S:11][C:10]2[N:9]3[C:12]([CH2:15]O)=[N:13][N:14]=[C:8]3[CH2:7][N:6]=[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:4]=2[CH:3]=1.C([N:26](CC)CC)C>C(Cl)(Cl)Cl>[NH2:26][CH2:15][C:12]1[N:9]2[C:10]3[S:11][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:6][CH2:7][C:8]2=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 213176872-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol

Product 1

HCID 191305Ro 11-7800

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

0.75 g of 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol is dissolved in 25 ml of absolute chloroform and there is added thereto 0.7 g of triethylamine and 0.6 g of methanesulphochloride. The mixture is stirred for 2.5 hours at 25° C., then washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulphate and evaporated. The resulting oily methanesulphonic acid ester of 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol is dissolved in 10 ml of dimethylformamide and the solution added dropwise at 0°-5° C. to a solution of 1 ml of liquid ammonia in 5 ml of dimethylformamide. The mixture is stirred for 2 hours at room temperature and then partitioned between saturated sodium chloride solution and methylene chloride. The organic phase is dried and evaporated and the residue recrystallized from ethanol. There is obtained 9-aminomethyl-2-chloro- 4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine of melting point 190°-192° C.

Workup

  1. additionthere is added
  2. washwashed twice with water and twice with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. dissolutionThe resulting oily methanesulphonic acid ester of 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol is dissolved in 10 ml of dimethylformamide
  6. additionthe solution added dropwise at 0°-5° C. to a solution of 1 ml of liquid ammonia in 5 ml of dimethylformamide
  7. stirringThe mixture is stirred for 2 hours at room temperature
  8. custompartitioned between saturated sodium chloride solution and methylene chloride
  9. customThe organic phase is dried
  10. customevaporated
  11. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-9f8f7102f23742b9901e0937a6fe86db
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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