Butyl isocyanate → HCID 4520152, compound

HRID 542490Notes

Reaction equation

HRID 542490 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12]([N:16]=[C:17]=[O:18])[CH2:13][CH2:14][CH3:15]>O1CCCC1>[CH2:12]([NH:16][C:17](=[O:18])[NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 8635Methyl Anthranilate

Product 1

HCID 4520152HCID 4520152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 13.55 gm of methyl anthranilate in 12 ml dry tetrahydrofuran, was added 8.9 ml of n-butyl isocyanate dropwise. The solution was stirred for 51/2 days and filtered. The filtrate was reduced to half of its original volume and further precipitated with hexane and filtered. The two residues were combined to yield the title compound as a white solid, m.p. 84°-85° C.; NMR(delta CDCl3): 0.79, 1.02 (m, 3H, CH3), 1.16-1.76 (m, 4H, CH2CH2), 3.27 (t, 2H, NCH2), 3.87 (s, 3H, OCH3), 4.82 (br, 1H, NH), 6.81-8.59 (m, 4H, ArH), 11.09 (s, 1H, NH). IR: 3305, 3260, 1708, 1642, 1560 cm-1.

Workup

  1. filtrationfiltered
  2. customfurther precipitated with hexane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e926a7a7999842c08aef8994744e70fb
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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