Chloroacetyl chloride → HCID 21502778, compound

HRID 1288560Notes

Reaction equation

HRID 1288560 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:23](C(C)C)CC)(C)C.[Cl:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl>[Cl:29][CH2:30][C:31]([NH:23][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:13][CH2:12][CH2:11]1)=[O:32]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 203266297,7-Diphenyl-1,4-oxazepane

Product 1

HCID 21502778HCID 21502778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 4.5 g of 7,7-diphenyl-hexahydro-1,4-oxazepine and 2.65 g of di-isopropyl-ethylamine in 30 ml of methylene chloride, that of 2.21 g of chloroactyl chloride in 25 ml of methylene chloride is added dropwise while stirring and cooling with ice. After stirring for 30 minutes at 0°-5°, the mixture is washed twice with 10 ml of cold N hydrochloric acid and 10 ml of cold 10% aqueous sodium carbonate each, dried, filtered and evaporated. The residue is triturated with diethyl ether and recrystallized from ethanol, to yield the 4-(2-chloroacetamido)-7,7-diphenyl-hexahydro-1,4-oxazepine melting at 150°-152°.

Workup

  1. temperaturecooling with ice
  2. stirringAfter stirring for 30 minutes at 0°-5°
  3. washthe mixture is washed twice with 10 ml of cold N hydrochloric acid and 10 ml of cold 10% aqueous sodium carbonate each,
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is triturated with diethyl ether
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0d17de9c8eea49cea2768df840ce258d
Source dataset
uspto-grants-1976_10
Patent number
US03988448

Reaction notes

Loading…