Methyl Isocyanate → HCID 70457674, compound

HRID 1981461Notes

Reaction equation

HRID 1981461 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)[OH:5].[CH3:19][N:20]=[C:21]=[O:22].C([O-])(=[O:25])C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>C(Cl)Cl>[CH3:19][NH:20][C:21]([O:25][N:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH:6]1[CH:4]([OH:5])[C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[Cl:1])=[O:22]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 13648577HCID 13648577, compound

Product 1

HCID 70457674HCID 70457674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(o-chloro-α-hydroxybenzyl)benzoxazole (3 g), methyl isocyanate (1.06 mL), a catalytic amount of dibutyltin diacetate and methylene chloride (50 mL) was stirred at room temperature in a pressure bottle overnight, after which the mixture was concentrated in vacuo. The solid residue was partititioned between ethyl acetate-diethyl ether and water. The organic extract was dried over Na2SO4, filtered and concentrated in vacuo to yield the corresponding carbamate. Recrystallization from toluene afforded 2.2 g of crystals, mp. 116°-117° C.

Workup

  1. concentrationafter which the mixture was concentrated in vacuo
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b61dfa892b24fef9c968be6f65c3405
Source dataset
uspto-grants-1986_06
Patent number
US04592774

Reaction notes

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