Triethylamine → HCID 19902169, compound

HRID 2372718Notes

Reaction equation

HRID 2372718 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14]O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:16])[CH:8]=2)[N:3]=1.S(Cl)(Cl)=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:11]2[CH2:14][CH2:13][N:12]=[C:10]2[C:9]2[CH:8]=[C:7]([F:16])[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 19902163HCID 19902163, compound

Product 1

HCID 19902169HCID 19902169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-chloro-6-fluoro-4-(2-hydroxyethylamino)quinazoline (7.0 g, 29 mmol) in dichloromethane (140 ml) was heated at reflux for 4 hours with thionyl chloride (4.2 ml, 58 mmol) and triethylamine (8 ml, 58 mmol). The cooled mixture was evaporated to dryness and extracted with water (80 ml). The acidic water solution was neutralized with 25% aqueous ammonia (approx. 7 ml) and the resulting precipitate was filtered off and dried to give the title compound as light yellow crystals, m.p. 209°-211° C.

Workup

  1. temperaturewas heated
  2. customThe cooled mixture was evaporated to dryness
  3. extractionextracted with water (80 ml)
  4. filtrationthe resulting precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-f372dbb21fb947f8b5b3fc2c031619f0
Source dataset
uspto-grants-1992_03
Patent number
US05100895

Reaction notes

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