Triethylamine → 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-chloroacetyl-N-methylcarbamate

HRID 1981291Notes

Reaction equation

HRID 1981291 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6](Cl)=[O:7])=[O:4].[CH3:10][C:11]1([CH3:21])[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19]([OH:20])[C:13]=2[O:12]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6](=[O:7])[O:20][C:19]1[C:13]2[O:12][C:11]([CH3:21])([CH3:10])[CH2:15][C:14]=2[CH:16]=[CH:17][CH:18]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 13424133N-chloroacetyl-N-methylcarbamoyl chloride

Product 1

HCID 134241342,3-dihydro-2,2-dimethyl-7-benzofuranyl N-chloroacetyl-N-methylcarbamateYield 79.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.0 g (0.006 m) of N-chloroacetyl-N-methylcarbamoyl chloride and 1.0 g (0.006 m) of 2,3-dihydro-2,2-dimethyl-7-benzofuranol in 15 cc dry toluene was stirred under nitrogen and 0.61 g (0.006 m) of triethylamine was added dropwise over a period of 10 mts. The mixture was stirred for an additional period of 2 hrs., filtered through a bed of celite and then the solvent was stripped off under reduced pressure to yield 1.39 g (yield 77%) of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-chloroacetyl-N-methylcarbamate, a light yellow oil. NMR (CDCl3): δ 7.3-6.6 (mn,3H); 4.75(s,2H); 3.40 (s,3H); 3.05 (s,2H) and 1.45 (s,6H). IR (CHCl3): ν1760 and 1725 cm-1

Workup

  1. stirringThe mixture was stirred for an additional period of 2 hrs
  2. filtration, filtered through a bed of celite

Sources & evidence

ORD record
ord-7a98c3ebda1e47a4a2ad8e902aa18edc
Source dataset
uspto-grants-1985_04
Patent number
US04514392

Reaction notes

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