Dimethylformamide → 2-Hydroxymethyl-3-triphenylmethylthiopyridine

HRID 2085989

反応式

HRID 2085989 の反応式
Cl.[SH:2][C:3]1[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.C(OCC)(=O)C>[C:22]1([C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[S:2][C:3]2[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 227269143-Mercapto-2-hydroxymethylpyridine hydrochloride

生成物 1

HCID 99080472-Hydroxymethyl-3-triphenylmethylthiopyridine収率 92.6%

試薬・触媒・溶媒 1

HCID 22728543Water ethylacetate溶媒

実験手順

Into a 3 L round bottom flask equipped with mechanical stirrer and nitrogen purge was charged 3-mercapto-2-hydroxymethylpyridine hydrochloride (25.0 g, 0.141 mol, 1 eq.) followed by DMF (1.2 L) and to the cloudy suspension was charged finely powdered potassium carbonate (58.5 g, 0.423 mol, 3.0 eq.). To the resulting solution was charged triphenylmethylchloride (38.1 g, 0.137 mol, 0.97 eq) and the reactions mixture was allowed to stir at room temperature for three hours until TLC analysis showed reaction completion (ethyl acetate-hexanes). The DMF solution was poured into 3 L of 4:1 water/ethyl acetate. The aqueous layer was separated and extracted an additional time with ethyl acetate (200 mL). The organics were combined and hexane (150 mL) was added. The organic layer was washed with water (2×200 mL) then brine (2×200 mL). The organic layer was dried with sodium sulfate, filtered and evaporated in vacuo to give 48.63 g of the title compound as a brown oil which was taken directly on to the next reaction. 1H NMR (CDCl3) δ 5.05 (s, 2H); 7.1-7.4 (m, 16H); 8.20 (d, 1H); 8.58 (d, 1H).

後処理

  1. customInto a 3 L round bottom flask equipped with mechanical stirrer
  2. customnitrogen purge
  3. customThe aqueous layer was separated
  4. extractionextracted an additional time with ethyl acetate (200 mL)
  5. additionhexane (150 mL) was added
  6. washThe organic layer was washed with water (2×200 mL)
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-b251c4454c5c45e7ba1fae44a5465536
出典データセット
uspto-grants-2004_04
特許番号
US06723716B1

関連ノート

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