Dimethylamine, hydrochloride → N,N-dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

HRID 1692030ノート

反応式

HRID 1692030 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.[CH3:15][NH:16][CH3:17].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.CN(C)C=O.ClCCl>[CH3:15][N:16]([CH3:17])[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]

参加物

8

反応物 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 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 18967003N,N-dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-Thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid (Example 92B, 394 mg, 2.02 mmol), dimethylamine hydrochloride (181 mg, 2.22 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (844 mg, 2.22 mmol) were combined in tetrahydrofuran (20 mL) and dimethylformamide (2 mL). Diisopropylethylamine (1.5 mL, 8.68 mmol) was added and the mixture was stirred at ambient temperature overnight. The 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%) to afford the title compound. MS (ESI+) m/z 222.9 (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%)

出典と根拠

ORDレコード
ord-8fd9e6c1d2d4409fa97702783c762dc5
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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