Aniline → HCID 131716909, compound

HRID 1493641Notes

Reaction equation

HRID 1493641 reaction equation
NC1C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+].Cl[CH2:31][C:32]([O:34][CH3:35])=[O:33]>C(#N)C.O>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH:24][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 7295Methyl chloroacetateHCID 516892Sodium BicarbonateHCID 19829944HCID 19829944, compound

Product 1

HCID 131716909HCID 131716909, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the aniline (Intermediate 87, 24.6 g, 107.3 mmol), sodium bicarbonate (13.5 g, 161 mmol) and methyl chloracetate (10.1 ml, 118 mmol) in acetonitrile (30 ml) was heated at 90°-100° for 48 h. Water (200 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating in vacuo to leave the crude product as a peach solid. Trituration with ether-hexane (1:1) gave the title compound (Intermediate 88) as a flesh coloured solid (30.3 g; 94%), m.p. 79°-81°.

Workup

  1. temperaturewas heated at 90°-100° for 48 h
  2. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  3. washThe combined extracts were washed with water (2×100 ml) and brine (100 ml)
  4. dry with materialbefore drying (Na2SO4)
  5. customevaporating in vacuo
  6. customto leave the crude product as a peach solid

Sources & evidence

ORD record
ord-00bee25155134c10b505dc40d709d3f5
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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