Triethylamine → N-ethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

HRID 1692032ノート

反応式

HRID 1692032 の反応式
[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:4]=2[O:3]1.Cl.[CH2:15]([NH2:17])[CH3:16].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1.ClCCl>[CH2:15]([NH:17][C:11]([C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2](=[S:1])[O:3][C:4]=2[CH:10]=1)=[O:13])[CH3:16]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 207347702-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

生成物 1

HCID 86631910N-ethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-Thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid (Example 92B, 424 mg, 2.17 mmol), ethanamine hydrochloride (266 mg, 3.26 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (991 mg, 2.61 mmol) were combined in tetrahydrofuran (5 mL). Triethylamine (1.4 mL, 977 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 1 N aqueous solution of hydrochloric acid, and absorbed on silica gel. The crude mixture was purified with silica gel chromatography eluting with a gradient of methanol in dichloromethane (2-20%). The chromatographed material was triturated with dichloromethane to afford the title compound. MS (ESI−) m/z 220.9 (M−H)−.

後処理

  1. washwashed with a 1 N aqueous solution of hydrochloric acid
  2. customabsorbed on silica gel
  3. customThe crude mixture was purified with silica gel chromatography
  4. washeluting with a gradient of methanol in dichloromethane (2-20%)
  5. customThe chromatographed material was triturated with dichloromethane

出典と根拠

ORDレコード
ord-3d9791f29cce4c49910e4e9805392d8c
出典データセット
uspto-grants-2012_04
特許番号
US08153813B2

反応ノート

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