Hexamethylenetetramine → HCID 22064400, compound

HRID 1828123Notes

Reaction equation

HRID 1828123 reaction equation
[CH2:1]1[N:6]2[CH2:7][N:8]3[CH2:10][N:4]([CH2:5]2)[CH2:3][N:2]1[CH2:9]3.[Cl:11][C:12]1[S:13][C:14]([CH2:17]Cl)=[CH:15][CH:16]=1>C(Cl)(Cl)Cl>[Cl:11][C:12]1[S:13][C:14]([CH2:17][CH:1]2[N:6]3[CH2:5][N:4]4[CH2:10][N:8]([CH2:9][N:2]2[CH2:3]4)[CH2:7]3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 5830792-Chloro-5-(chloromethyl)thiophene

Product 1

HCID 22064400HCID 22064400, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of hexamethylenetetramine (HMTA) (3.12 g, 22.2 mmol) in CHCl3 (35 mL) was added 2-chloro-5-chloromethylthiophene (1.02 mL, 8.46 mmol). The reaction mixture was heated at reflux for 4 hr, cooled, and filtered to give white solid 5-chloro-2-[(1,3,5,7-tetraazatricyclo-[3.3.1.1 (3,7)]decyl) methyl]thiophene (2.28 g, 88%). ES-MS (M)+=271, 273 (Cl). 1H-NMR (DMSO-d6): δ 4.27 (s, 2H), 4.39–4.57 (ABq, 6H), 5.06 (s, 6H), 7.21–7.24 (ABq, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hr
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-bb4166706f8942ad939415635cbab85b
Source dataset
uspto-grants-2006_06
Patent number
US07056926B2

Reaction notes

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