Diisopropylethylamine → 2-Chloro-5-(isocyanatomethyl)thiophene

HRID 1685083Notes

Reaction equation

HRID 1685083 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[S:18][C:17]([CH2:19][NH2:20])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:13][C:14]1[S:18][C:17]([CH2:19][N:20]=[C:2]=[O:4])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 11446421(5-Chlorothiophen-2-yl)methanamine

Product 1

HCID 545954932-Chloro-5-(isocyanatomethyl)thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphosgene (1.15 g, 3.9 mmol) in CH2Cl2 (30 mL) was added dropwise a mixture of (5-chlorothiophen-2-yl)methanamine (1.14 g, 7.8 mmol) and DIPEA (2.0 g, 15.6 mmol) in CH2Cl2 (32 mL) over 2 hours at 0 C under N2 atmosphere. After addition was complete, the mixture was refluxed for 1 hour and then cooled to ambient temperature. The mixture was washed with aq. KHSO4, brine, dried over Na2SO4, and concentrated to give 5-chlorothiophen-2-yl-methyl isocynate a yellow liquid (1.34 g, yield 100%), which was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for 1 hour
  3. washThe mixture was washed with aq. KHSO4, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b6924ca86554f28a96b602e3ea6eb6b
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

Loading…