Benzyl chloroformate → HCID 54095129, compound

HRID 614011Notes

Reaction equation

HRID 614011 reaction equation
[C:1]1([CH2:7][O:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[O:21][CH:20]([CH3:22])[CH2:19][C:18]2=[C:23]([NH2:25])[CH:24]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[C:1]1([CH2:7][O:8][C:9](=[O:10])[NH:25][C:23]2[C:18]3[CH2:19][CH:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([O:14][CH3:13])[CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 21329810HCID 21329810, compound

Product 1

HCID 54095129HCID 54095129, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.65 grams of phenylmethylchlorocarbonate are dripped at 5° C. into a stirred mixture containing 0.7 grams of 2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine hydrochloride, 5 cc of 2N NaOH and 10 cc of chloroform. When the addition is terminated vigorous stirring is continued for one hour at the same temperature and for two hours at room temperature. Then the organic phase is separated, washed with water, dried over Na2SO4 and concentrated to dryness. The obtained residue crystallized twice from ethyl ether-petroleum ether yields 0.9 grams (88 percent of theoretical) of (2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)carbamic acid phenylmethyl ester which melts at 82°-83° C.

Workup

  1. customare dripped at 5° C. into a stirred mixture
  2. additionWhen the addition
  3. customis terminated vigorous
  4. customThen the organic phase is separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe obtained residue crystallized twice from ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-e8c9cc50071e4f128dba6e7020f9a557
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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