Methanethioamide → 2-Guanidino-4-(4-thiazolyl)thiazole dihydrobromide

HRID 280735

반응식

HRID 280735 반응식
[BrH:1].[Br:2][CH2:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]([NH2:14])=[NH:13])[S:9][CH:10]=1)=O.[CH:15]([NH2:17])=[S:16]>CN(C)C=O>[BrH:2].[BrH:1].[NH:11]([C:8]1[S:9][CH:10]=[C:6]([C:4]2[N:17]=[CH:15][S:16][CH:3]=2)[N:7]=1)[C:12]([NH2:14])=[NH:13]

참가 물질

4

반응물 2

HCID 3005587MethanethioamideHCID 178419719HCID 178419719, 화합물

생성물 1

HCID 1784192712-Guanidino-4-(4-thiazolyl)thiazole dihydrobromide수율 86.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1.8 g (5.2 mmol) of 2-bromo-1-(2-guanidino-4-thiazolyl)ethanone hydrobromide, 0.34 g (5.5 mmol) of thioformamide, and 10 ml of dimethylformamide was stirred at room temperature for 2 hours. The mixture was concentrated and the residue was triturated with acetonitrile. The resulting precipitate was collected by filtration, washed with acetonitrile, and dried to afford 1.74 g (85%) of 2-guanidino-4-(4-thiazolyl)thiazole dihydrobromide. Th:s was dissolved in 10 ml of water, and 1 ml of saturated sodium bicarbonate solution was added. The resulting precipitate was collected by filtration, washed well with water, then acetonitrile, then dried in vacuo to afford 1.17 g of 2-guanidino-4-(4-thiazoyl)thiazole as a white solid, mp 220°-222°; nmr (DMSO-d6) (δ): 8.96 (s, 1H); 7.96 (s, 1H); 7.18 (s, 1H); 7.0 (b, 4H); calcd. for C7H7N5S2 : C, 37.32; H, 3.13; N, 31.09; found: 36.94; H, 3.52; N, 29.74.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with acetonitrile
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with acetonitrile
  5. customdried

출처 및 근거

ORD 기록
ord-f508f44100a44422b6dd008b86fcffd9
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590299

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