Formamide → HCID 17990151, compound

HRID 222009Notes

Reaction equation

HRID 222009 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].C([O-])=O.[NH4+].[CH:24]([NH2:26])=O>>[O:15]1[CH2:16][CH2:17][O:18][C:14]21[CH2:13][CH2:12][C:5]1[C:6]3[C:7](=[O:8])[NH:26][CH:24]=[N:1][C:2]=3[S:3][C:4]=1[CH2:19]2

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 10902110Ethyl 2-amino-4,7-dihydro-5H-spiro[1-benzothiophere-6,2'-[1,3]dioxolane]-3-carboxylate

Product 1

HCID 17990151HCID 17990151, compoundYield 88%

Conditions

Temperature
140 °C

Procedure

To a stirring solution of ethyl 2-amino-4,7-dihydro-5H-spiro[1-benzothiophene-6,2′-[1,3]dioxolane]-3-carboxylate (40.0 g, 0.142 mol) in formamide (225 mL) was added ammonium formate (17.8 g, 0.282 mol). The resulting mixture was stirred with at 140° C. for 16 h, after which time the heterogeneous contents were removed from heating, and allowed to cool to rt. The contents were filtered, the solid filter cake was washed with water (2×60 mL), and suction dried overnight to afford the desired product as an off-white solid (33.0 g, 88%). 1H-NMR (DMSO-d6) δ 12.35 (broad s, 1H), 8.00 (s, 1H), 3.92 (s, 4H), 2.95 (t, 2H), 2.91 (s, 2H), 1.83 (t, 2H); LCMS RT=1.87 min; [M+H]+=265.2.

Workup

  1. customafter which time the heterogeneous contents were removed
  2. temperaturefrom heating
  3. temperatureto cool to rt
  4. filtrationThe contents were filtered
  5. filtrationthe solid filter cake
  6. washwas washed with water (2×60 mL), and suction
  7. customdried overnight

Sources & evidence

ORD record
ord-b0aec80939bc484490271172548c4ed3
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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