Water → HCID 54297524, compound

HRID 223201Notes

Reaction equation

HRID 223201 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][S:13][C:9]=3[C:8](=[O:14])[N:7]3[CH2:15][CH2:16][CH2:17][C@H:6]3[C:5]=12.[Cl:18]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:18][C:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][S:13][C:9]=3[C:8](=[O:14])[N:7]3[CH2:15][CH2:16][CH2:17][C@H:6]3[C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 53687465HCID 53687465, compound

Product 1

HCID 54297524HCID 54297524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 (12.2 mmol) of (S)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one in 20 ml of dimethylformamide are stirred at 65° for 40 minutes with 1.63 g (12.2 mmol) of N-chlorosuccinimide. The solution is poured into water and extracted with chloroform. The organic phase is washed several times with water, dried over magnesium sulphate and evaporated. By column chromatography on silica gel there is obtained (S)-1-chloro-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8 one of melting point 180°-183°.

Workup

  1. extractionextracted with chloroform
  2. washThe organic phase is washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-ef89f064bb7c49f38d320acbb12b15f4
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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