Triethylamine → HCID 11047717, compound

HRID 1381572Notes

Reaction equation

HRID 1381572 reaction equation
C(N(CC)CC)C.[Br:8][CH2:9][CH2:10][N:11]([CH2:25][CH2:26][Br:27])[C:12]1[CH:17]=[CH:16][C:15]([NH:18]C(NCCBr)=O)=[CH:14][CH:13]=1>CCOCC>[Br:8][CH2:9][CH2:10][N:11]([CH2:25][CH2:26][Br:27])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 15597312HCID 15597312, compound

Product 1

HCID 11047717HCID 11047717, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2HCl (2.93 g) was reacted with triethylamine (2.90 g) in ether (150 ml). The reaction mixture was filtered, and β-bromoethyl isocyanate (1.23 g) was added to the filtrate to give a white solid (3.32 g; melting point 103°-105° C.). The infrared absorption spectrum of the solid was as shown in FIG. 2. It was very similar to the infrared absorption spectrum of N-[p-bis(β-chloroethyl)aminophenyl]-N'-(β'-chloroethyl)urea obtained in Example 1, and showed a strong absorption based on the NH linkage at 3300 cm-1 and a strong absorption based on the carbonyl linkage of the ureido group at 1625 cm-1. The elemental analysis values were C 33.44%, H 3.47%, and N 8.84% which agreed with the calculated values for the composition formula C13H18N3OBr3 (472.04) which were C 33.908%, H 3.84%, N 8.90%. Its mass spectrum showed M⊕ at m/e=472 and peaks corresponding to [M⊕ -Br] at m/e=393 and 392. The foregoing results clearly show that the resulting white solid is N-[p-bis(β-bromoethyl)aminophenyl]-N'-(β'-bromoethyl)urea (designated as compound No. 1). The yield was 95.0%. ##STR13##

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionβ-bromoethyl isocyanate (1.23 g) was added to the filtrate
  3. customto give a white solid (3.32 g; melting point 103°-105° C.)
  4. customThe infrared absorption spectrum of the solid
  5. customa strong absorption
  6. customa strong absorption
  7. customThe foregoing results clearly

Sources & evidence

ORD record
ord-9f318cb2963a486aa57c5fa1fcdf60e5
Source dataset
uspto-grants-1989_02
Patent number
US04803223

Reaction notes

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