2-Chloroethyl isocyanate → HCID 20333751, compound

HRID 1706612Notes

Reaction equation

HRID 1706612 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:6]=2[CH:19]=1.[Cl:20][CH2:21][CH2:22][N:23]=[C:24]=[O:25]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:24]([NH:23][CH2:22][CH2:21][Cl:20])=[O:25])[CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 20333776HCID 20333776, compound

Product 1

HCID 20333751HCID 20333751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 Parts of 7-chloro-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine is dissolved in 250 parts by volume of methylene chloride. To this solution 15 parts of 2-chloroethylisocyanate is slowly added with stirring. The resultant mixture is stirred at ambient temperature for about 90 minutes. The resulting dark brown solution is filtered through a layer of activated magnesium silicate, the filtrate dried and treated with charcoal. After removal of charcoal by filtration the solvent is removed from the resultant filtrate to affort an oil. This oil is dissolved in about 100 parts by volume of ether and the resultant solution cooled to give 7-chloro-N-(2-chloroethyl)-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide as crystalline solid melting at about 150°-153° C. This compound is represented by the following formula ##STR19##

Workup

  1. filtrationThe resulting dark brown solution is filtered through a layer of activated magnesium silicate
  2. customthe filtrate dried
  3. additiontreated with charcoal
  4. customAfter removal of charcoal
  5. filtrationby filtration the solvent
  6. customis removed from the resultant filtrate
  7. dissolutionThis oil is dissolved in about 100 parts by volume of ether
  8. temperaturethe resultant solution cooled

Sources & evidence

ORD record
ord-a49e2a0f5a0640a3931594b8ed461a72
Source dataset
uspto-grants-1980_06
Patent number
US04208327

Reaction notes

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