Methyl Isocyanate → HCID 70373622, compound

HRID 1087730Notes

Reaction equation

HRID 1087730 reaction equation
[CH:1]1[C:13]2[O:12][N:11]=[C:6]3[N:7]=[CH:8][CH2:9][O:10][C:4]([C:5]=23)=[CH:3][CH:2]=1.[H-].[Na+].[CH3:16][N:17]=[C:18]=[O:19]>CN(C)C=O>[CH3:16][NH:17][C:18]([C:3]1[CH:2]=[CH:1][C:13]2[O:12][N:11]=[C:6]3[N:7]=[CH:8][CH2:9][O:10][C:4]=1[C:5]=23)=[O:19]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 70362693HCID 70362693, compound

Product 1

HCID 70373622HCID 70373622, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 4,5-dihydroisoxazolo[3,4,5-ef][1,4]benzoxazepine of Example 7(b) (3.7 g; 21.0 mmole) in 60 ml dimethylformamide (DMF) was added to a suspension of sodium hydride (1.2 g; 25.2 mmole) in DMF. After 15 minutes, a solution of methylisocyanate in 15 ml DMF was added. The reaction was quenched into a dilute solution of HCl and extracted thrice with ethyl acetate. The organics were washed with water and dried (saturated NaCl solution, MgSO4). The desired urea was purified via flash chromatography (6% ethylacetate/dichloromethne) to give a solid which was triturated with pentane to give 2.4 g (49%) of 4,5-dihydro-3-methylaminocarbonylisoxazolo[3,4,5-ef][1,4]benzoxazepine, mp 177°-179.5° C.

Workup

  1. customThe reaction was quenched into a dilute solution of HCl
  2. extractionextracted thrice with ethyl acetate
  3. washThe organics were washed with water
  4. dry with materialdried (saturated NaCl solution, MgSO4)
  5. customThe desired urea was purified via flash chromatography (6% ethylacetate/dichloromethne)
  6. customto give a solid which
  7. customwas triturated with pentane

Sources & evidence

ORD record
ord-1133fa1cb30e41f4940c7ecfd0f531bc
Source dataset
uspto-grants-1990_10
Patent number
US04960767

Reaction notes

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